Deep River holiday rentals

We found 447 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:13 Nov - 20 Nov

Interior
Outdoor patio fireplace, patio heaters.
Pool
Private kitchen
Exceptional
(54 reviews)

Resort style getaway w/pool, spa, game room & more

East Haddam

8% off
AU$10,587
for 7 nights, 1 home
AU$1,512 per night
includes taxes & fees
Resort style getaway w/pool, spa, game room & more
Living area
Exterior
Room
Interior
Exceptional
(67 reviews)

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

Westbrook

8% off
AU$9,934
for 7 nights, 1 home
AU$1,419 per night
includes taxes & fees
Brand New, Villa Je t’aime, Across the Street from the beach, Sleeps 6 adults
Beach
Exterior
Living area
Exterior detail
Wonderful
(58 reviews)

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

Old Lyme

8% off
AU$3,593
for 7 nights, 1 cottage
AU$513 per night
includes taxes & fees
2bdr Beachfront; 11A first floor; Old Colony Beach, Old Lyme CT
Exterior
Interior
Private kitchen
Living area
Exceptional
(30 reviews)

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Durham

8% off
AU$7,462
for 7 nights, 1 home
AU$1,066 per night
includes taxes & fees
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Living Room
Front of House
Side of House with outdoor shower to rinse off from the beach.
Kitchen
Exceptional
(11 reviews)

4 BED/2 BATH -PRIVATE BEACH: OLD COLONY

Old Lyme

7% off
AU$6,691
for 7 nights, 1 home
AU$956 per night
includes taxes & fees
4 BED/2 BATH -PRIVATE BEACH: OLD COLONY
Parlor by fireplace
Inner Hall
Whitefield Rock and rear view of Ludington House (Whitefield Suite is at left)
Entry Hall
Exceptional
(20 reviews)

Ludington House, Historic CT Shoreline Mansion filled with luxury and antiques

Old Lyme

10% off
AU$21,082
for 7 nights, 1 home
AU$3,012 per night
includes taxes & fees
Ludington House, Historic CT Shoreline Mansion filled with luxury and antiques
Living area
Living area
Dining
Interior
Exceptional
(11 reviews)

Sunny, Beach Days - Enjoy the beach just steps away in Clinton, Connecticut

Clinton

8% off
AU$7,331
for 7 nights, 1 home
AU$1,047 per night
includes taxes & fees
Sunny, Beach Days - Enjoy the beach just steps away in Clinton, Connecticut
Room
Terrace/patio
Private kitchen
Exterior
Exceptional
(31 reviews)

Updated cottage "Beriozka" on Cedar Lake

Chester

7% off
AU$2,301
for 7 nights, 1 cottage
AU$329 per night
includes taxes & fees
Updated cottage "Beriozka" on Cedar Lake
Outdoor dining
Living area
Living area
Room
Exceptional
(19 reviews)

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

Colchester

8% off
AU$3,987
for 7 nights, 1 home
AU$570 per night
includes taxes & fees
Room for the whole family 1/2 hour to Mohegan and Mystic Seaport
Interior
Living area
Front of Historic Mansion B&B
Dining
Exceptional
(5 reviews)

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

Higganum

8% off
AU$2,532
for 7 nights, 1 room
AU$362 per night
includes taxes & fees
Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance
Loft View of Living Room
Exterior
Living Room with view of expandable dining table
Dining
Exceptional
(89 reviews)

Cozy cottage near downtown Clinton, Marina & Hammonasset Park

Clinton

7% off
AU$2,072
for 7 nights, 1 cottage
AU$296 per night
includes taxes & fees
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Dining
Property grounds
Private kitchen
Level 2 (240V/40amp) EV charger available
Exceptional
(11 reviews)

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

Higganum

16% off
AU$4,661
for 7 nights, 1 home
AU$666 per night
includes taxes & fees
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
Exterior detail
Interior
Interior
Room
Exceptional
(140 reviews)

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Old Saybrook

8% off
AU$4,894
for 7 nights, 1 home
AU$699 per night
includes taxes & fees
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Interior
Backyard
Room
Entrance is on the front of the building.
Exceptional
(8 reviews)

The Little Chestnut. A charming historic apartment in Downtown Chester

Chester

7% off
AU$2,240
for 7 nights, 1 apartment
AU$320 per night
includes taxes & fees
The Little Chestnut. A charming historic apartment in Downtown Chester
Winter blaze
Winter afternoon from the boathouse
Full chef's kitchen with new appliances
Ipe deck in the morning sun
Exceptional
(6 reviews)

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

Old Lyme

16% off
AU$5,951
for 7 nights, 1 home
AU$850 per night
includes taxes & fees
Gracious Riverfront Home where the Connecticut River and Long Island Sound Meet
One full bedroom w two full sleeper sofas to accommodate 4 guests comfortably.
Property grounds
Property grounds
Exceptional
(63 reviews)

Summer at the Haddam House

Haddam

8% off
AU$2,580
for 7 nights, 1 home
AU$369 per night
includes taxes & fees
Summer at the Haddam House
Newly remodeled kitchen
Beautiful sun room for dining
Private kitchen
family room
Exceptional
(26 reviews)

Make Memories in Charming Hawk's Nest Beach!

Old Lyme

8% off
AU$3,584
for 7 nights, 1 home
AU$512 per night
includes taxes & fees
Make Memories in Charming Hawk's Nest Beach!
Front of Birdsong at end of summer
Pathway leading to Birdsong- spring
Livingroom and Kitchen
Kitchen and living room
Exceptional
(92 reviews)

Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town

Madison

12% off
AU$2,031
for 7 nights, 1 apartment
AU$290 per night
includes taxes & fees
Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town
Living area
Exterior
Exterior detail
Beach
Exceptional
(53 reviews)

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

Old Lyme

8% off
AU$2,811
for 7 nights, 1 cottage
AU$402 per night
includes taxes & fees
2Bdr Beachfront; 11B second floor, Old Colony Beach , CT
Chef's kitchen with cooking supplies, large island, and ample cabinet space.
Enter into the open floor plan with updated kitchen, living, and family room.
Covered patio is well lit with overhead lighting.
Seat 6 people at the dining table, or use it to get some work done.
Exceptional
(79 reviews)

UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge

Westbrook

8% off
AU$4,656
for 7 nights, 1 home
AU$665 per night
includes taxes & fees
UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge
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    Enjoy full kitchens, laundry, pools, gardens and more
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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)
  • Harvey's Beach (7.8 mi / 12.6 km)
  • Hammonasset Beach (8.6 mi / 13.8 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 most popular type of holiday home accommodation in Deep River?
According to our data, houses are the most popular type of holiday property in Deep River. But as you'd expect, everyone's idea of an awesome trip differs. Stayz has holiday homes in a variety of sizes and shapes, and we'll help you locate the perfect fit for you.
How much does it cost to rent a holiday home in Deep River?
Season, property type and length of stay are some things that can determine the price of a holiday home. Simply click on your travel dates to find your ideal escape. From comfy cabins to expansive luxury villas, all Stayz holiday homes offer unbeatable value.
How much does it cost to rent a beach house in Deep River?
Prices for beach houses in Deep River vary depending on the style and size of the property and when you're travelling. Just enter your travel dates into Stayz and how many guests to see your options and prices. From there you can use our filters to narrow down your search by amenities, nearby activities, ratings and more.
What are popular home amenities in Deep River?
A garden is one of the more preferred amenities people search for in Deep River. Whatever style of holiday home you're planning to book, they all offer perks to make your stay more convenient and comfortable.
What are the top attractions for families in Deep River?
Keep the kids busy at these fantastic family-friendly attractions in Deep River:
  • Essex Steam Train
  • Harveys Beach
  • Clinton Town Beach
How old do you have to be to rent a holiday home in Deep River?
It's advisable to check with the Deep River holiday home you're looking at on Stayz as the age limit varies. However, typically it's 16, 18 or 21.
How long can I rent a holiday home in Deep River for?
It all depends on the Deep River property. To view all available options offering extended stays, just type your dates and number of guests into Stayz. You can enjoy having the property to yourself, as well as comforts such as a full kitchen, air conditioning and a backyard where the little ones can play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

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