Deep River holiday rentals

We found 450 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Deep River to find one that's perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you expect for your stay, which might include Wi-Fi and a pool. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Deep River

Showing deals for:25 Dec - 1 Jan

Dining
Exterior
Interior
Living area
Exceptional
(68 reviews)

Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults

Westbrook

8% off
AU$10,014
for 7 nights, 1 home
AU$1,431 per night
includes taxes & fees
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
Exterior
Exterior
Exterior detail
Beach
Wonderful
(59 reviews)

2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT

Old Lyme

8% off
AU$3,622
for 7 nights, 1 cottage
AU$517 per night
includes taxes & fees
2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT
Aerial view of back deck area
Front of House
Kitchen
Living Room
Exceptional
(11 reviews)

4 BED/2 BATH -PRIVATE BEACH: OLD COLONY

Old Lyme

7% off
AU$6,922
for 7 nights, 1 home
AU$989 per night
includes taxes & fees
4 BED/2 BATH -PRIVATE BEACH: OLD COLONY
Outdoor dining
Living area
Living area
Interior
Exceptional
(19 reviews)

Room for the whole family 1/2 hour to Mohegan and Mystic Seaport

Colchester

8% off
AU$4,641
for 7 nights, 1 home
AU$663 per night
includes taxes & fees
Room for the whole family 1/2 hour to Mohegan and Mystic Seaport
Entryway 🐳
Property grounds
Kitchen
Dining
Exceptional
(17 reviews)

Cornfield Point Cottage

Old Saybrook

8% off
AU$11,528
for 7 nights, 1 home
AU$1,647 per night
includes taxes & fees
Cornfield Point Cottage
Interior
Living area
Bedroom with 2 single Beds
Dining
Exceptional
(6 reviews)

Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance

Higganum

8% off
AU$2,552
for 7 nights, 1 room
AU$365 per night
includes taxes & fees
Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance
3 season porch with couch, 2 upholstered chairs and coffee table
Property grounds
Private kitchen
Level 2 (240V/40amp) EV charger available
Exceptional
(13 reviews)

Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger

Higganum

16% off
AU$4,782
for 7 nights, 1 home
AU$683 per night
includes taxes & fees
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
Ipe deck in the morning sun
Winter afternoon from the boathouse
Full chef's kitchen with new appliances
Living area
Exceptional
(6 reviews)

Gracious Riverfront Home where the Connecticut River and Long Island Sound Meet

Old Lyme

16% off
AU$8,508
for 7 nights, 1 home
AU$1,215 per night
includes taxes & fees
Gracious Riverfront Home where the Connecticut River and Long Island Sound Meet
Room
Beach
Living area
Private kitchen
Exceptional
(35 reviews)

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL

Clinton

12% off
AU$6,593
for 7 nights, 1 home
AU$942 per night
includes taxes & fees
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
Room
Property grounds
One full bedroom w two full sleeper sofas to accommodate 4 guests comfortably.
Private kitchen
Exceptional
(68 reviews)

Summer at the Haddam House

Haddam

8% off
AU$2,624
for 7 nights, 1 home
AU$375 per night
includes taxes & fees
Summer at the Haddam House
Beach
Exterior
Living area
Exterior detail
Exceptional
(56 reviews)

2Bdr Beachfront; 11B second floor, Old Colony Beach , CT

Old Lyme

8% off
AU$2,833
for 7 nights, 1 cottage
AU$405 per night
includes taxes & fees
2Bdr Beachfront; 11B second floor, Old Colony Beach , CT
Dining
Dining
Room
Exterior
Exceptional
(47 reviews)

Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️

Westbrook

8% off
AU$4,559
for 7 nights, 1 home
AU$651 per night
includes taxes & fees
Sea Salt Air Changes Everything - ⭐️Stroll to Private Association Beach⭐️

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Why visit Deep River

  • Scenic River Views: Deep River is beautifully situated along the Connecticut River, offering stunning vistas and peaceful spots for relaxation.
  • Historic Landmarks: The town boasts charming historic houses that reflect its rich heritage and architectural appeal.
  • Outdoor Adventures: Visitors can explore serene parks and engage in various outdoor activities like hiking and picnicking.
  • Local Culture: Experience the friendly atmosphere through local markets and community events that showcase Deep River's culture.
  • Family-Friendly Atmosphere: Deep River is ideal for families, with plenty of attractions and activities suitable for all ages.

Popular types of accommodation in Deep River

Discover Deep River, Connecticut, a charming city offering scenic river views, historic landmarks and a host of family-friendly attractions. Whether you’re after private holiday homes, cosy cottages, or modern apartments, Deep River holiday rentals cater for every taste. Enjoy exploring local campgrounds and pet friendly hotels that ensure a memorable stay in this delightful destination.

  • Private Holiday Homes: Embrace the comfort and privacy of fully-equipped homes, ideal for families and groups looking for a homely holiday retreat.
  • Cottages: Enjoy the charm and quaint appeal of cottages, offering a cosy escape with a touch of rustic elegance.
  • Apartments: Experience the convenience of modern apartments, perfect for those seeking a self-catering urban stay.
  • Cabins: Relish the simplicity and tranquillity of cabins, providing an intimate connection with nature.
  • Villas: Indulge in the luxury of spacious villas, designed for a refined and relaxing holiday experience.**

Top attractions near Deep River

Deep River offers a charming retreat with scenic beauty and captivating outdoor experiences, perfect for a romantic getaway or a cultural adventure. Enjoy the historic houses, explore the national state park, and relax by the beach as you delve into the local culture. Discover the enchanting experience of visiting Deep River, where natural beauty and history come together for an unforgettable holiday.

  • Westbrook Town Beach: A serene and inviting beach offering soft sand, perfect for sunbathing and relaxation. The calm waters are great for swimming, making it an ideal spot for families and beach lovers.
  • Lake Hayward: This picturesque lake boasts stunning scenery and a romantic atmosphere. It’s perfect for outdoor activities such as boating, fishing, and picnicking amidst nature’s beauty.
  • Harvey's Beach: A charming beach with a relaxed vibe, featuring gentle waves and ample space for beach games. It's a delightful location for enjoying a sunny day by the water.

Things to do recommended for couples

Deep River offers a charming escape for couples. Explore the scenic Connecticut River by taking a romantic boat cruise, or enjoy a leisurely walk through the picturesque streets. Don't miss a visit to local wineries for a delightful tasting experience, perfect for creating lasting memories together.

Things to do recommended for families

Families visiting Deep River can enjoy a delightful day exploring local parks, engaging in interactive museum exhibits, and partaking in scenic river walks, ensuring a memorable experience for both children and adults.

Things to do recommended for groups

Experience the thrill of motor racing at Waterford Speedbowl, located 26km from Deep River. This venue offers an adrenaline-fuelled atmosphere perfect for group travellers seeking excitement and adventure together.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Deep River

If you’re travelling with a group, family, or pets, or if you’re seeking longer stays, be sure to refine your search based on your key preferences. Here are some helpful booking tips for your Stayz experience.

  • Traveling to Deep River with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor area for group gatherings. Thankfully, you can easily refine your search on Stayz to include all of these options and more.
  • Traveling to Deep River with young kids: Traveling with young children can be demanding. You must prioritise their comfort and safety, ensuring they have access to age-appropriate facilities, such as a private swimming pool. It is also advisable to consider your closeness to attractions that are suitable for families.
  • Taking your pets with you to Deep River: For many, a family holiday isn’t truly fulfilled without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Deep River: If you're searching for holiday rentals with offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Deep River

Deep River, Connecticut, offers a charming escape for those seeking outdoor adventures and romantic scenery. Nestled along the picturesque Connecticut River, visitors can explore serene parks and enjoy scenic views. The town is known for its friendly atmosphere, making it ideal for families and budget travellers alike. Whether you're strolling through the local market or soaking in the natural beauty of the area, Deep River promises a delightful holiday experience filled with warmth and scenic charm.

  • Old Saybrook: A charming city nestled 11km away from Deep River, Old Saybrook offers a delightful blend of outdoor pursuits, scenic vistas and romantic escapes. Visitors are drawn to its inviting recreational areas and well-kept golf courses, where one can enjoy a leisurely day outdoors. The local beaches, including a family-friendly stretch and a national state park, provide ideal settings for a peaceful stroll or a picnic with a view of the serene seascape.
  • Westbrook: Located 10km from Deep River, Westbrook is a vibrant city that promises an enriching outdoor and romantic experience, coupled with captivating scenery. The area is known for its varied attractions, from exhilarating music concerts to engaging golf courses and cultural events. Its family beach and event conference venue offer a blend of leisure and community spirit, making it a perfect destination for a memorable day out.
  • Madison: Situated 11km from Deep River, Madison is a delightful city acclaimed for its outdoor adventures and scenic landscapes. It offers a range of activities from invigorating recreational pursuits to challenging golf courses and lively music concerts. The nearby national state park and family beach add to the appeal, providing scenic spots that capture the essence of a picturesque and adventurous holiday.

Best time to go to Deep River

If you're planning a trip to Deep River, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.3°F (-0.4°C)Light RainMostly SunnySlightly LowModerately Low
February32.4°F (0.2°C)Light RainMostly SunnyAverageModerately Low
March38.5°F (3.6°C)Light RainMostly SunnyAverageModerately Low
April48.2°F (9.0°C)Light RainMostly SunnySlightly HighAverage
May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
June66.4°F (19.1°C)Light RainMostly SunnySlightly HighModerately High
July73.8°F (23.2°C)Light RainMostly SunnySlightly HighModerately High
August72.7°F (22.6°C)Light RainMostly SunnyAverageModerately High
September66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
October56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
November45.5°F (7.5°C)Light RainMostly SunnySlightly LowAverage
December37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage

Booking with Stayz is a breeze

Looking to cut costs on your upcoming journey? Consider remaining flexible with your travel dates, as prices do vary. Additionally, booking a longer stay often results in significant savings. To find the ideal Stayz property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s pioneering Trip Board offers you a dedicated area to initiate new journeys, resume previous plans, or organise your itineraries. Properties you have saved or booked can now be found under Potential, Upcoming, or Current Trips. To access Trip Boards, please visit: https://www.stayz.com.au/trips

**Based on Vrbo properties bookings.

Book a holiday rental for your Deep River getaway

The parks and surrounding scenery provide a peaceful ambience to your holiday home in Deep River. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Deep River

Do you want to discover attractions to visit while you're in the area? Venture out of your cosy holiday rental and experience everything that Deep River has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Chatfield Hollow State Park (5.5 mi / 8.9 km)
  • Machimoodus State Park (9.1 mi / 14.6 km)
  • Dinosaur Place at Nature's Art (14.4 mi / 23.2 km)
  • Powder Ridge Mountain Park and Resort (16.2 mi / 26.2 km)
  • Brownstone Exploration & Discovery Park (16.7 mi / 26.9 km)
  • Chamard Vineyards (5.4 mi / 8.7 km)

Exploring the natural landscape of Deep River

Whether you're an adventurous traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Deep River. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Chatfield Hollow State Park (5.5 mi / 8.9 km)
  • Westbrook Town Beach (6.2 mi / 10 km)
  • Clinton Town Beach (6.9 mi / 11.1 km)
  • Goose Island (7.3 mi / 11.7 km)
  • Chalker Beach (7.3 mi / 11.8 km)
  • Harvey's Beach (7.8 mi / 12.6 km)

Transport options to and around Deep River

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 22.1 mi (35.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into New London, CT (GON-Groton - New London), which is 22.9 mi (36.8 km) away.

Frequently asked questions

What is the best area to stay in Deep River when booking a holiday rental?
When considering the best area to stay in Deep River, Connecticut, you'll want to explore the charm of the Main Street area. This quaint neighbourhood offers a delightful mix of local shops and eateries, giving visitors a taste of small-town life. One of the highlights of this area is the picturesque Deep River Landing Park, where you can enjoy scenic views along the Connecticut River, superb for a leisurely stroll or a picnic. Additionally, the nearby Goodspeed Opera House is a must-visit for those interested in the performing arts, showcasing a variety of productions throughout the year.In terms of holiday rentals, Deep River has a modest selection of properties that cater to different tastes and group sizes, ensuring a comfortable stay for visitors.
What is the most popular type of holiday rental accomodation in Deep River?
In Deep River, holiday houses are the most popular type of holiday rental, with several available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces such as gardens or patios, making them ideal for families or groups seeking a comfortable stay.
Are there pet-friendly house rentals in Deep River?
In Deep River, Connecticut, there are several pet-friendly house rentals available that cater to travellers looking for a comfortable stay. Many of these rentals typically feature amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can roam freely.The area offers a charming, small-town atmosphere with close proximity to various parks and natural attractions. For pet owners, nearby spots like the Deep River Landing or the picturesque Essex Town Park provide opportunities for leisurely walks and outdoor activities with furry companions.
Are there any remote work holiday rentals in Deep River?
In Deep River, Connecticut, there are several remote work holiday rentals available that cater to those looking to blend work and leisure. The area is known for its picturesque landscapes and charming small-town atmosphere, making it an appealing location for remote workers. Many of these properties offer essential amenities such as reliable Wi-Fi and designated workspaces, allowing guests to maintain productivity during their stay.The town features lovely surroundings, including the Connecticut River, where you can enjoy scenic views and outdoor activities during breaks from work. Additionally, local cafes and parks provide great spots for leisurely walks or casual meetings. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Deep River?
In Deep River, popular rental amenities include pet-friendly options, making it convenient for travellers who wish to bring their pets along. Many holiday rentals feature decks or patios, allowing guests to enjoy the serene surroundings and fresh air. A fireplace is a common amenity, providing warmth and a cosy atmosphere during chilly evenings. Additionally, these rentals often accommodate service animals and include WiFi, ensuring connectivity for those who need to stay online.
When is the best time to visit Deep River for a holiday rental?
The peak travel season in Deep River runs from May to July, making it an ideal time for those looking to enjoy the charm of this picturesque Connecticut town. With warm temperatures typically ranging from 15 to 30 degrees Celsius, visitors can take full advantage of outdoor activities, from boating on the Connecticut River to exploring local parks and quaint shops.July stands out as the most popular month to visit, attracting travellers. The lively option during this time is great for those who enjoy community events and festivals, all set against the backdrop of summer's vibrancy.If you're considering a more budget-friendly option, November offers a quieter yet equally enchanting experience. The changing autumn leaves create a stunning landscape, great for scenic walks and enjoying the peaceful ambience that Deep River is known for.No matter when you choose to visit, Deep River has a wealth of experiences to offer, ensuring your stay will be enjoyable and memorable.
What are the top attractions in Deep River?
In Deep River, visitors can experience firsthand the charm of this picturesque New England town. One of the top attractions is the Deep River Historical Society, where guests can learn about the local history and heritage through engaging exhibits. The nearby Essex Steam Train offers a delightful ride through scenic landscapes, great for families and history enthusiasts alike.Nature lovers can explore the beautiful hiking trails at the nearby Cockaponset State Forest, which provides opportunities for hiking and observing local wildlife. Additionally, the scenic Connecticut River, with its opportunities for boating and fishing, is a highlight for outdoor enthusiasts.For a taste of local culture, the town hosts various events throughout the year, including the Deep River Ancient Mariner's annual Fourth of July celebration, which features parades and fireworks.
Are all fees included in the Deep River 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 Deep River holiday homes with parking?
Stayz offers a wide selection of holiday homes in Deep River 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 Deep River holiday homes?
You can find great discounts on holiday homes in Deep River 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 Deep River holiday home booking on Stayz?
To find Deep River 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 Deep River?
A long-stay holiday home in Deep River 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 Deep River holiday home?
Book your Deep River 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 Deep River?
Prices for holiday homes in Deep River 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 Deep River 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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