Otis holiday rentals

We found 551 holiday rentals — enter your dates for availability
Select from 17 homes, 10 cottages and other holiday rentals in Otis to find one that's perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the amenities that you expect and more, such as parking and air conditioning. At the end of the day, you'll find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Otis

Showing deals for:20 Nov - 27 Nov

Dining room with butcher block table
Terrace/patio
Screened in porch
Property grounds
Exceptional
(102 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
AU$3,942
for 7 nights, 1 home
AU$563 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Living area
Interior
Private kitchen
Interior
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

8% off
AU$4,873
for 7 nights, 1 home
AU$696 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
Outdoor spa tub
Exterior
Interior
Living area
Exceptional
(21 reviews)

Beautiful Home in AMAZING Berkshire Location

Lee

8% off
AU$6,219
for 7 nights, 1 home
AU$888 per night
includes taxes & fees
Beautiful Home in AMAZING Berkshire Location
Living area
Private kitchen
Property grounds
Exterior
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
AU$7,753
for 7 nights, 1 home
AU$1,108 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Enclosed porch- view into back yard- dining/game table
Kitchen with counter seating for 4- door on the right to garage
View from entry into living room- perfect spot for relaxing!
Outdoor dining
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
AU$5,578
for 7 nights, 1 home
AU$797 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Welcome Home!
The open-concept living space seamlessly blends the comfort of the living room with the functionality of the kitchen, all adorned by a double sided
Unwind and cherish moments together in the inviting warmth of the cozy living room.
Add a touch of warmth and charm to your dining experience!
Exceptional
(7 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
AU$7,971
for 7 nights, 1 home
AU$1,139 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Living area
Interior
Exterior
Dining
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
AU$3,783
for 7 nights, 1 cabin
AU$540 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
The living room flows into the dining room.
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
(41 reviews)

An In-Town Beauty with Late Checkout

Great Barrington

8% off
AU$4,994
for 7 nights, 1 home
AU$713 per night
includes taxes & fees
An In-Town Beauty with Late Checkout
Back Porch
Living Room
Front Gardens
Property grounds
Exceptional
(27 reviews)

Secluded Family Home in Serene Stockbridge Woods

Stockbridge

8% off
AU$4,372
for 7 nights, 1 home
AU$625 per night
includes taxes & fees
Secluded Family Home in Serene Stockbridge Woods
Blue House side entry from driveway
River view from window
dining area
Great room river view
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

8% off
AU$3,536
for 7 nights, 1 home
AU$505 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Kitchen with Dining Area - well-equipped and great layout
Living Room - Queen Sleep Sofa (First Floor)
Backyard
Dining Room - table expands to seat 10
Exceptional
(10 reviews)

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

9% off
AU$4,032
for 7 nights, 1 home
AU$576 per night
includes taxes & fees
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Open and bright main floor living space with stunning views of Laurel Lake.
Open kitchen area with bar seating, great for socializing while you meal prep.
Open kitchen w/ bar & high top seating- sliding door access to second story deck
Second story deck with lake views, dining table for 8, sitting area and grill
Exceptional
(30 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

16% off
AU$5,446
for 7 nights, 1 home
AU$778 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
Interior
Terrace/patio
Interior
Exterior
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
AU$3,431
for 7 nights, 1 cottage
AU$490 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Kitchen
Interior
Interior
Kitchen
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
AU$5,412
for 7 nights, 1 home
AU$773 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Private kitchen
Interior
Living area
Room
Exceptional
(56 reviews)

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Great Barrington

12% off
AU$1,657
for 7 nights, 1 apartment
AU$237 per night
includes taxes & fees
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Private kitchen
Ultimate Relaxation! The hot tub will be warm and waiting for your arrival
Open floor plan, natural light in a stylish space
Welcome Home!
Exceptional
(8 reviews)

Best of the Berkshires + Hot Tub by Evergreen Home

Great Barrington

11% off
AU$4,265
for 7 nights, 1 home
AU$609 per night
includes taxes & fees
Best of the Berkshires + Hot Tub by Evergreen Home
Kitchen open to living room
Kitchen
2nd bedroom
Patio off kitchen
Exceptional
(77 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

New Marlborough

8% off
AU$2,304
for 7 nights, 1 cottage
AU$329 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
Interior
Property grounds
Exterior
Room
Wonderful
(6 reviews)

The Serendipity Spot

Great Barrington

7% off
AU$1,982
for 7 nights, 1 apartment
AU$283 per night
includes taxes & fees
The Serendipity Spot
Custom Chef's Kitchen with high end appliances from Bertazzoni and Fisher & Paykel
Private kitchen
Quarter & Rift sawn white oak floors
Dining
Exceptional
(11 reviews)

The Penthouse, Downtown Lenox by Evergreen Home

Lenox

11% off
AU$6,590
for 7 nights, 1 apartment
AU$941 per night
includes taxes & fees
The Penthouse, Downtown Lenox by Evergreen Home
Exterior
Outdoor dining
Private kitchen
Private kitchen
Exceptional
(12 reviews)

Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!

Monterey

8% off
AU$3,914
for 7 nights, 1 home
AU$559 per night
includes taxes & fees
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Come and unwind.
Porch opens up from dining room. Ceiling fan and lights above.
View of the river.
Entrance view.
Exceptional
(42 reviews)

Converted Berkshire schoolhouse on a quiet river

New Marlborough

8% off
AU$2,846
for 7 nights, 1 home
AU$407 per night
includes taxes & fees
Converted Berkshire schoolhouse on a quiet river

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

Take in the natural beauty of Otis

The parks and surrounding scenery provide a peaceful ambience to your holiday home in Otis. One of the city's many top draws is its skiing. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Otis

Are you looking for attractions to see during your stay? Venture out of your cosy holiday rental and experience everything that makes Otis a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Otis Ridge (0.5 mi / 0.8 km)
  • Ski Butternut (11.7 mi / 18.9 km)
  • Wyndhurst Golf & Club (13.7 mi / 22 km)
  • Kennedy Park (16 mi / 25.7 km)
  • Hotchkiss Mobile Studio (17.1 mi / 27.6 km)
  • The Ranch Golf Club (17.7 mi / 28.5 km)

Exploring the natural landscape of Otis

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Otis is a great place to spend some time outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Otis Reservoir (3.9 mi / 6.3 km)
  • Tolland State Forest (4.1 mi / 6.6 km)
  • Lake Garfield (5.4 mi / 8.8 km)
  • Goose Pond Reservation (7.9 mi / 12.7 km)
  • Lake Buel (9.6 mi / 15.4 km)
  • Littleville Lake (12 mi / 19.4 km)

Transport to and around Otis

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 19 mi (30.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Westfield, MA (BAF-Barnes Municipal), which is 19.2 mi (30.9 km) away.

Frequently asked questions

Where are the best areas for renting a beach house in Otis?
For renting a beach house in Otis, Massachusetts, the most appealing area is around the picturesque Otis Reservoir, which is a popular spot for both swimming and boating. Properties near the waterfront often come with amenities such as private docks, outdoor decks, and spacious patios, superb for enjoying summer evenings by the water. Many of these rentals also feature fully equipped kitchens and open-plan living spaces, ideal for families or groups looking to gather and relax.The nearby town of Blandford offers additional options, where you can find charming cabins and cottages set in a more wooded environment, providing a sense of privacy and tranquillity. These properties frequently come with amenities like fire pits, picnic areas, and easy access to hiking trails, making them great for nature enthusiasts.Additionally, the surrounding areas provide a wealth of outdoor activities, including fishing, hiking, and exploring local parks. Rentals in this region often highlight the serene natural beauty of the Berkshires, with some properties offering stunning views of the landscape, ensuring a peaceful retreat for travellers looking to escape the hustle and bustle of everyday life.
Where are the best Otis ski resort rentals?
For ski resort rentals near Otis, Massachusetts, the closest skiing options can be found at Butternut Basin in Great Barrington, which is roughly a 30-minute drive away. In Great Barrington, travellers can find a variety of holiday rentals that cater to skiers. Many properties are conveniently located just a short drive from the slopes and offer amenities such as spacious living areas, wood-burning fireplaces, and fully equipped kitchens, making them great for families or groups planning to enjoy a ski getaway.Additionally, the nearby town of Lee offers charming accommodations, including historic homes and modern cabins. These rentals often feature outdoor spaces for relaxation, game rooms, and hot tubs, providing comfort after a day on the mountain. The area is also known for its beautiful natural surroundings, with opportunities for hiking and exploring the scenic Berkshire landscape.For those interested in dining and shopping, both Great Barrington and Lee have a selection of local restaurants and shops, enhancing the overall experience for travellers in search of both winter sports and a quaint New England atmosphere.
What is the most popular type of holiday rental accomodation in Otis?
In Otis, holiday houses are the most popular type of holiday rental, with around 56 available throughout the area. These properties typically come with spacious living areas, fully equipped kitchens, and often feature outdoor spaces such as decks or gardens, ideal for enjoying the serene surroundings. Additionally, there are approximately 40 cottages that provide a charming and cosy atmosphere, often with rustic decor and amenities that enhance the home-from-home experience. For those seeking a more rustic retreat, several cabins and chalets are also available, superb for immersing oneself in nature.
Are there any family house rentals in Otis?
In Otis, Massachusetts, there are numerous family-friendly house rentals available, with around 26 options to choose from. This charming area is known for its natural beauty, making it an excellent destination for families seeking outdoor adventures. Many of the properties feature spacious living areas, fully equipped kitchens ideal for preparing family meals, and outdoor spaces where children can play and explore.Visitors can enjoy amenities such as Wi-Fi, air conditioning, and access to private outdoor areas, which are superb for relaxation after a day of activities. The locale is close to several points of interest, including the picturesque Otis Reservoir, where families can partake in swimming, kayaking, and fishing. Additionally, the nearby state forests offer hiking trails and opportunities for wildlife viewing, ensuring that there's plenty to keep everyone entertained.
Can I rent a holiday home with a pool or hot tub in Otis?
In Otis, Massachusetts, there are several holiday homes available for rent that feature pools and hot tubs, offering a relaxing getaway in a serene setting. The area is known for its beautiful natural surroundings, including nearby lakes and forests, making it ideal for outdoor enthusiasts. Many of the properties come equipped with private pools, hot tubs, and spacious outdoor areas, great for enjoying warm summer days or unwinding after a day of exploring. Travellers can also expect amenities such as fully equipped kitchens for self-catering, comfortable living spaces, and some rentals may include additional features like barbecue grills and fire pits, enhancing the overall holiday experience.
Are there pet-friendly house rentals in Otis?
In Otis, Massachusetts, there are several pet-friendly house rentals available for those looking to enjoy a getaway with their furry companions. Many of these properties are located in serene surroundings, offering amenities such as spacious backyards, fully equipped kitchens, and comfortable living spaces, great for families or groups.The area is close to the beautiful Otis Reservoir, which is ideal for outdoor activities like swimming, fishing, and kayaking, providing ample opportunities for pets to enjoy the great outdoors. Additionally, the nearby hiking trails in the surrounding Berkshire region offer scenic walks where pets are often welcome, making it a fantastic destination for nature lovers and their pets.
Are there any remote work holiday rentals in Otis?
In Otis, Massachusetts, there are numerous remote work-friendly holiday rentals available, with around 108 options to choose from. This picturesque town, located in the Berkshires, offers a serene environment for those looking to balance work and leisure. Many properties come equipped with amenities tailored for remote work, including high-speed internet, desks, and comfortable office chairs, ensuring a productive workspace.Travellers can enjoy the natural beauty of the area, with nearby attractions such as Otis Reservoir, which provides opportunities for fishing, boating, and hiking. Properties often feature spacious living areas, full kitchens for convenient meal preparation, and outdoor spaces to relax after a long day. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Otis?
In Otis, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, as well as decks or patios that provide outdoor space for relaxation and enjoying the natural surroundings. Many properties also feature fireplaces, superb for cozy evenings, and onsite parking for convenience.
When is the best time to visit Otis for a holiday rental?
The best time to visit Otis for a holiday rental is during the peak season from June to August. This vibrant period attracts families and outdoor enthusiasts, eager to embrace the warm weather and explore the natural beauty that Otis has to offer. With temperatures typically ranging from the mid-teens to mid-twenties Celsius, it's an excellent time for swimming, hiking, and enjoying various water sports on the serene lakes.July, in particular, stands out as the most popular month, bustling with activity and a lively option. Visitors can enjoy local festivals, farmers' markets, and countless opportunities for outdoor adventures. The longer daylight hours allow for ample time to appreciate the area's scenic landscapes, making it an ideal choice for those who love to be outdoors.For those seeking a more budget-friendly experience, November is a wonderful option to consider. While it's outside the high tourist season, this month boasts its own charm, with cooler temperatures averaging around 5 to 10 degrees Celsius. You can enjoy the tranquil beauty of Otis in the fall, with fewer crowds and the chance to witness the stunning autumn foliage.
What are the top attractions in Otis?
In Otis, Massachusetts, visitors can enjoy a variety of outdoor attractions that highlight the area's natural beauty. The main draw is the picturesque Otis Reservoir, great for swimming, boating, and fishing, with nearby picnic areas for family gatherings. The surrounding woods offer excellent opportunities for hiking and nature walks, making it a great spot for outdoor enthusiasts.For those interested in history, the local Otis Town Hall is an interesting site, reflecting the area's rich heritage. The nearby Berkshire Mountains provide additional recreational activities, such as skiing in the winter and hiking during the warmer months.Additionally, the quaint charm of the local community can be experienced through various seasonal events and farmers' markets, allowing visitors to immerse themselves in the local culture and enjoy fresh produce.
Are all fees included in the Otis 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 Otis holiday homes with parking?
Stayz offers a wide selection of holiday homes in Otis 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 Otis holiday homes?
You can find great discounts on holiday homes in Otis 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 Otis holiday home booking on Stayz?
To find Otis 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 Otis?
A long-stay holiday home in Otis 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 Otis holiday home?
Book your Otis 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 Otis?
Prices for holiday homes in Otis 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 Otis 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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