Photo by Caitlin Reese

Richmond holiday rentals

We found 808 holiday rentals — enter your dates for availability
Discover a selection of 20 homes and other holiday rentals in Richmond that are perfect for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the best amenities for hanging out with the people that matter most, including air conditioning and cable TV. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Richmond

Showing deals for:18 Dec - 25 Dec

Interior
Terrace/patio
Dining
Interior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
AU$3,413
for 7 nights, 1 cottage
AU$488 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
View from the lawn by the water
view from the 2nd bedroom
Workstation with a view!
Open plan dining area with water views and access to the sunroom
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
AU$7,977
for 7 nights, 1 home
AU$1,140 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Open kitchen to great room, wonderful for cooking and entertaining
The great room with wonderful water views and working fireplace
Hot tub overlooking the lake
Dining
Exceptional
(86 reviews)

Spectacular setting on your own private lake close to it all!

Lee

8% off
AU$6,469
for 7 nights, 1 home
AU$924 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Property grounds
Private kitchen
Terrace/patio
Exterior
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
AU$7,993
for 7 nights, 1 home
AU$1,142 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Outdoor dining
Living area
Interior
Exterior detail
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
AU$6,327
for 7 nights, 1 home
AU$904 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Kitchen with stainless steel appliances
Fully screened porch!
Front Staircase
Reading nook with natural lighting
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Pittsfield

12% off
AU$5,164
for 7 nights, 1 home
AU$738 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
A mudroom off the back leads to the large wooden deck
You will love dining and working in this rich and colorful room
Staircase
Outdoor dining and grill on the 16' x 20' wooden deck.
Exceptional
(43 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
AU$5,464
for 7 nights, 1 home
AU$781 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Living area
Interior
Dining
Property grounds
Exceptional
(8 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,788
for 7 nights, 1 cabin
AU$541 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Open kitchen w/ bar & high top seating- sliding door access to second story deck
Open kitchen area with bar seating, great for socializing while you meal prep.
Open and bright main floor living space with stunning views of Laurel Lake.
Living room with fireplace and forest views
Exceptional
(31 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

16% off
AU$5,453
for 7 nights, 1 home
AU$779 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Room
Interior
Interior
Exterior
Exceptional
(42 reviews)

A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.

Stephentown

8% off
AU$2,395
for 7 nights, 1 home
AU$342 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Private kitchen
Outdoor dining
Exterior detail
Dining
Exceptional
(11 reviews)

Berkshires Getaway Walk to Distillery - No Pet Fee!

Sheffield

8% off
AU$4,026
for 7 nights, 1 home
AU$575 per night
includes taxes & fees
Berkshires Getaway Walk to Distillery - No Pet Fee!
Queen bedroom
Terrace/patio
Property grounds
Dining room with butcher block table
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

9% off
AU$3,970
for 7 nights, 1 home
AU$567 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Never miss a thing with this expansive open concept kitchen and living room
After a hard day on the trails or a long day on the town, relax in this oasis
Seamless entertaining with the wide open concept, living room -kitchen- patio
Enjoy a beautiful crisp night under the lights
Exceptional
(29 reviews)

Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.

Great Barrington

6% off
AU$6,450
for 7 nights, 1 home
AU$921 per night
includes taxes & fees
Adventure Ready Ranch Sleeps 10 & 0.7 mi to GB Main St. Wi-Fi + HOT TUB.
View from ski room to trail thru woods to Grouse Run - fantastic location!!
Spring at Jiminy Peak 2019
Country Inn heated pool & outdoor hot tub is open all year. Towels are provided
Night skiing view from living room
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

13% off
AU$12,684
for 7 nights, 1 home
AU$1,812 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Entrance into house with wood burning stove to right and staircase
View from 2nd floor balcony (after leaves have fallen)
Large Smart HDTV with electric fireplace in living room, showing dining room
Views from the back of the 16 acres on the property
Exceptional
(73 reviews)

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Hancock

12% off
AU$3,552
for 7 nights, 1 home
AU$507 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
Alfresco dining
River view from window
Great room river view
Blue House side entry from driveway
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

8% off
AU$3,824
for 7 nights, 1 home
AU$546 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Terrace/patio
Living area
Private kitchen
Living area
Exceptional
(8 reviews)

Modern Log Chalet - 10 acres, views, and a pond!

Chatham

8% off
AU$5,507
for 7 nights, 1 home
AU$787 per night
includes taxes & fees
Modern Log Chalet - 10 acres, views, and a pond!
Kitchen
Interior
Interior
Kitchen
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
AU$5,420
for 7 nights, 1 home
AU$774 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Private kitchen
Interior
Exterior
Living area
Exceptional
(61 reviews)

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington

12% off
AU$1,649
for 7 nights, 1 apartment
AU$236 per night
includes taxes & fees
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Interior
Property grounds
We highly recommend the Sauna
After a day in the snow
Exceptional
(14 reviews)

Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.

Sheffield

12% off
AU$3,484
for 7 nights, 1 home
AU$498 per night
includes taxes & fees
Secluded Mountainside House with Outdoor Sauna, Surrounded by Trees.
Private kitchen
Outdoor dining
Exterior
Private kitchen
Exceptional
(13 reviews)

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

Monterey

8% off
AU$3,893
for 7 nights, 1 home
AU$556 per night
includes taxes & fees
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
another view of same bedroom as well as makeup table
new backyard table
Beaver Pond Pool/clubhouse
kitchen and laundry room area
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Hancock

23% off
AU$5,025
for 7 nights, 1 apartment
AU$718 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Welcome Home!
Ultimate Relaxation! The hot tub will be warm and waiting for your arrival
Open floor plan, natural light in a stylish space
Dining Area, view into living room. Games, books, records all available for your enjoyment!
Exceptional
(9 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
AU$4,670
for 7 nights, 1 home
AU$667 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
view into large bathroom
Dining
Living Room, wow!
Interior
Exceptional
(17 reviews)

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond

17% off
AU$3,496
for 7 nights, 1 apartment
AU$499 per night
includes taxes & fees
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

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    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Travel to relaxing Richmond

Enjoy the wineries and other features of Richmond. This city's horse riding, mountain views and restaurants attract many visitors, as does its relaxing and welcoming location. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Richmond

Are you looking for things to do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Richmond has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Bousquet Ski Area (5.4 mi / 8.6 km)
  • Wyndhurst Golf & Club (5.5 mi / 8.9 km)
  • Jiminy Peak Mountain Resort (13.2 mi / 21.2 km)
  • Ski Butternut (13.4 mi / 21.5 km)
  • Catamount Ski Area (15.3 mi / 24.7 km)
  • Furnace Brook Winery at Hilltop Orchards (1.7 mi / 2.8 km)

Exploring the natural features in Richmond

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Richmond is a great place to get outside. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Stockbridge Bowl (3.6 mi / 5.8 km)
  • Lenox Mountain (3.7 mi / 6 km)
  • The Mount (5 mi / 8.1 km)
  • Berkshire Botanical Garden (5.2 mi / 8.4 km)
  • Naumkeag Museum (6.3 mi / 10.2 km)
  • Goose Pond Reservation (11.1 mi / 17.9 km)

How to get to and around Richmond

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 5.3 mi (8.5 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Hudson, NY (HCC-Columbia County), which is 18.4 mi (29.7 km) away.

Frequently asked questions

What is the best area to stay in Richmond when booking a holiday rental?
When considering a holiday rental in Richmond, Massachusetts, the area around the picturesque Richmond Village is a fantastic option. This charming neighbourhood offers a unique blend of natural beauty and local culture, making it an ideal spot for visitors looking to immerse themselves in the serene landscape of the Berkshires.Richmond Village is known for its close proximity to the stunning October Mountain State Forest, which provides a range of outdoor activities such as hiking, biking, and birdwatching. Additionally, the nearby Berkshire Botanical Garden is a delightful attraction, showcasing beautiful flora and offering a peaceful retreat for nature lovers.While the exact number of holiday rental properties may vary, this area typically features a selection of lovely homes and cabins that cater to different tastes and budgets. Staying in Richmond allows you to enjoy the tranquil atmosphere while still being within easy reach of the vibrant arts scene and dining options found in nearby towns.
Where are the best areas for renting a beach house in Richmond?
For renting a beach house in Richmond, Massachusetts, the areas along the coastline offer some delightful options. The nearby Cape Ann region, particularly around the town of Rockport, features picturesque beaches like Long Beach and Bearskin Neck. Here, you can find charming seaside cottages that often come with amenities such as private decks, outdoor grills, and spacious living areas, great for enjoying the coastal breezes and sunsets.Another excellent choice is the vicinity of the Parker River National Wildlife Refuge, which provides access to pristine beaches and scenic landscapes. Rentals in this area typically have features like fully equipped kitchens, laundry facilities, and sometimes even access to outdoor showers for rinsing off after a day at the beach. The proximity to nature trails and birdwatching opportunities makes it an attractive spot for nature enthusiasts.Moreover, the local area boasts quaint shops and seafood restaurants, adding to the overall experience. Many beach houses in Richmond and its surroundings are designed for comfort, offering amenities that cater to families or groups seeking a relaxing getaway by the water.
Where are the best Richmond ski resort rentals?
For ski resort rentals near Richmond, Massachusetts, travellers should consider the nearby area of the Berkshires, particularly around the town of Lenox and the Pine Grove area. These locations offer convenient access to popular ski resorts such as Jiminy Peak, which is only a short drive away. In Lenox, visitors can find a range of accommodations, including cosy cabins and spacious chalets that often come equipped with amenities like hot tubs, fireplaces, and fully stocked kitchens, superb for unwinding after a day on the slopes.Additionally, properties in these areas typically provide easy access to local attractions, including the enchanting landscapes of the Berkshire Mountains and the cultural offerings of nearby towns. Many rentals feature outdoor spaces for guests to enjoy the fresh mountain air, and some even have options for indoor recreation, such as game rooms or home theatres.For those looking to explore beyond skiing, the Berkshires offer a wealth of hiking trails and scenic vistas. Accommodations in towns like Stockbridge and Great Barrington may also include rustic lodges or boutique inns, often with amenities like complimentary breakfast, free Wi-Fi, and convenient proximity to local dining and shopping options.
What is the most popular type of holiday rental accomodation in Richmond?
In Richmond, holiday houses are the most popular type of holiday rental accommodation, with about 60 available throughout the area. These spacious properties typically feature multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking to enjoy the natural beauty of the surroundings. Additionally, there are around 12 charming cottages that provide a quaint and cosy atmosphere, superb for a more intimate getaway. While there are several apartments, they are not as prevalent as the holiday houses and cottages.
Are there any family house rentals in Richmond?
In Richmond, Massachusetts, there are family-friendly house rentals available, with around 14 options to choose from. This charming area offers a picturesque backdrop, ideal for families looking to enjoy nature and outdoor activities. Many properties feature spacious living areas, fully equipped kitchens great for family meals, and outdoor spaces for kids to play and explore.Visitors can take advantage of nearby attractions like the scenic Richmond Pond, which provides opportunities for swimming and picnicking, as well as hiking trails that wind through the stunning landscapes of the Berkshires. Furthermore, the local area is known for its welcoming community and access to various recreational activities, ensuring a memorable stay for families venturing to this lovely part of Massachusetts.
Can I rent a holiday home with a pool or hot tub in Richmond?
In Richmond, Massachusetts, there are several holiday homes available for rent that feature pools or hot tubs, making it an appealing destination for those seeking relaxation and leisure. The area is known for its picturesque landscapes and tranquil surroundings, providing a great backdrop for a getaway. Travellers can expect amenities such as private pools, hot tubs, spacious outdoor areas for sunbathing or barbecuing, and fully equipped kitchens for convenient meal preparation. Some properties may also include additional features like fire pits and comfortable lounge areas, ideal for family gatherings or socialising with friends.
Are there pet-friendly house rentals in Richmond?
In Richmond, Massachusetts, there are numerous pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these holiday homes feature amenities such as spacious yards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Some properties may also include outdoor spaces like decks or patios, superb for enjoying the serene surroundings.The town is surrounded by natural beauty, with opportunities for outdoor activities such as hiking and exploring nearby state parks. Richmond's location also allows easy access to local attractions and scenic spots, adding to the appeal of the area for those looking to combine a tranquil getaway with outdoor adventures.
Are there any remote work holiday rentals in Richmond?
In Richmond, Massachusetts, there are approximately 80 remote work-friendly holiday rentals available, making it a great choice for those looking to combine work and leisure. Many of these properties are equipped with essential amenities for remote work, including high-speed internet, designated desk spaces, and comfortable office chairs, ensuring a productive environment.The area is surrounded by beautiful natural landscapes, providing opportunities for outdoor activities during breaks, such as hiking in the nearby Berkshire Mountains or exploring local parks. Additionally, Richmond's charming small-town atmosphere offers a relaxed setting, with local eateries and shops that can be easily accessed. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Richmond?
In Richmond, popular rental amenities typically include kitchens, allowing guests to prepare their own meals, which is especially convenient for families or groups. Many properties also feature outdoor spaces such as decks or patios, superb for enjoying the fresh air and relaxing after a day of exploring the area. Onsite parking is another sought-after amenity, providing ease of access for those travelling by car. Additionally, some rentals may come equipped with items like blenders, suiting those who enjoy making smoothies or other blended drinks.
When is the best time to visit Richmond for a holiday rental?
The best time to visit Richmond, Massachusetts, for a holiday rental is during the peak season from July to September. This vibrant period attracts many visitors seeking outdoor adventures, including hiking, cycling, and exploring the picturesque landscapes that the region has to offer. July, in particular, is the most popular month, when the weather is warm and inviting, making it ideal for enjoying the natural beauty of the Berkshires.During this time, temperatures typically range from 15 to 30 degrees Celsius, providing comfortable conditions for outdoor activities and sightseeing. The lush greenery and stunning vistas create a superb backdrop for leisure walks, picnics, and family gatherings. Richmond's proximity to various hiking trails and scenic spots allows easy access to a variety of outdoor experiences.For those looking for a more budget-friendly option, consider visiting in December. While this is outside the peak tourist season, Richmond transforms into a charming winter wonderland, offering unique opportunities for a peaceful retreat amidst the festive atmosphere. The lower tourist traffic allows you to enjoy the local sights at a leisurely pace and discover the beauty of Richmond in a quieter setting.
What are the top attractions in Richmond?
In Richmond, Massachusetts, visitors can enjoy the serene beauty of the Berkshires, which is known for its stunning landscapes and outdoor recreational opportunities. One of the top attractions in the area is the nearby Mount Greylock State Reservation, where guests can explore hiking trails that offer breathtaking views from the highest peak in Massachusetts.The town itself features quaint local shops and art galleries, providing a charming atmosphere for leisurely strolls. For those interested in history, the nearby town of Stockbridge is home to the Norman Rockwell Museum, showcasing the works of the famous American artist.Nature enthusiasts may also appreciate the proximity to the Appalachian Trail, which runs through the region and offers ample opportunities for hiking and experiencing the natural beauty of western Massachusetts.
Are all fees included in the Richmond holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Richmond holiday homes with parking?
Stayz offers a wide selection of holiday homes in Richmond with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Richmond holiday homes?
You can find great discounts on holiday homes in Richmond on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Richmond holiday home booking on Stayz?
To find Richmond holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Richmond?
A long-stay holiday home in Richmond is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Richmond holiday home?
Book your Richmond holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Richmond?
Prices for holiday homes in Richmond vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Richmond to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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