A mountainous landscape with rocky outcrops and autumn-colored trees.

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Coastal Connecticut holiday rentals

View from property

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (181 reviews)
"Great property for quiet and a nice getaway. Great little places to eat and shop in the surrounding towns."
United States
Frank
The price is ฿4,471
฿8,188 total
includes taxes & fees
17 Sept - 18 Sept
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Classic Suite | Iron/ironing board, free WiFi, bed sheets

2. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (107 reviews)
"The property is clean and very nice"
United States
Nisse
The price is ฿5,837
฿8,733 total
includes taxes & fees
13 Sept - 14 Sept
DUNE Fairfield Beach
House (4 Bedrooms) | Interior

3. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home
3.0 star property
Tunxis Hill
The price is ฿15,101
฿24,820 total
includes taxes & fees
18 Sept - 19 Sept
4 Mi to Beach & Dtwn! Charming Fairfield Home
Front of property

4. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is ฿26,913
฿42,515 total
includes taxes & fees
23 Aug - 24 Aug
Beechmont - Perfect for Family Retreat!
Standard Room, 1 King Bed, Main Building | Property entrance

5. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is ฿7,252
฿8,340 total
includes taxes & fees
20 Aug - 21 Aug
Guesthouse at Norwalk Inn
Exterior

6. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (161 reviews)
"The front desk gentleman that checked us in was excellent!!"
United States
Selena
The price is ฿4,318
฿4,966 total
includes taxes & fees
20 Aug - 21 Aug
Stamford Suites
Cottage (2 Bedrooms) | Interior

7. Montville Retreat Near Mohegan Sun: 2-home Bundle!

Montville Retreat Near Mohegan Sun: 2-home Bundle!
3.0 star property
Montville
The price is ฿23,214
฿38,343 total
includes taxes & fees
26 Aug - 27 Aug
Montville Retreat Near Mohegan Sun: 2-home Bundle!
Apartment (0 Bedroom) | Interior

8. Cozy Studio: Indoor Hot Tub & Inground Pool Access

Cozy Studio: Indoor Hot Tub & Inground Pool Access
3.0 star property
Montville
10.0 out of 10, Exceptional, (1 review)
"Everything from the price,location,tranquility, and the host Allen was awesome. We would go back in a heartbeat. Montville is beautiful."
United States
Eduardo
The price is ฿6,278
฿14,192 total
includes taxes & fees
26 Aug - 27 Aug
Cozy Studio: Indoor Hot Tub & Inground Pool Access
Apartment (1 Bedroom) | Interior

9. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is ฿4,692
฿9,579 total
includes taxes & fees
24 Aug - 25 Aug
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Condo | Terrace/patio

10. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (285 reviews)
"Great place!"
United States
Christine
The price is ฿10,127
฿14,516 total
includes taxes & fees
7 Sept - 8 Sept
Cliffside Resort Condominiums
Flat-screen TV

11. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (48 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is ฿10,616
฿12,129 total
includes taxes & fees
7 Sept - 8 Sept
North Fork Resort
Lobby

12. Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,388 reviews)
"Property and room very clean Friendly staff and plenty of parking"
United States
Amelia
The price is ฿9,813
฿11,859 total
includes taxes & fees
7 Sept - 8 Sept
Montauk Manor
Luxury Apartment | In-room dining

13. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is ฿29,738
฿38,044 total
includes taxes & fees
20 Aug - 21 Aug
3BR Prime Luxury NY - Free Parking
Luxury House | Living area

14. Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is ฿28,251
฿36,529 total
includes taxes & fees
24 Aug - 25 Aug
Two Wash
One Bedroom Residence King with Ocean View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

15. Offshore Spa & Residences

Offshore Spa & Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (3 reviews)
"What a memorable way to celebrate America’s 250th Anniversary and the Fourth of July at Offshore Montauk. The festive atmosphere, beautiful weather, beach days, and fireworks made for an unforgettable getaway. The property is beautifully designed with thoughtful room layouts, high-end appliances, and quality finishes that create a luxurious yet comfortable experience. The attention to detail throughout the property is impressive, and it's exciting to see the continued improvements being...
United States
Frank
The price is ฿28,221
฿36,018 total
includes taxes & fees
8 Sept - 9 Sept
Offshore Spa & Residences
Apartment | Living area

16. The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (293 reviews)
"Found mold under the pull-out couch"
United States
Anna
The price is ฿10,893
฿14,677 total
includes taxes & fees
9 Sept - 10 Sept
The Surf Club
Apartment | Iron/ironing board, free WiFi

17. Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (444 reviews)
"The location is amazing, and the customer service is excellent. Unfortunately, the mattress and the air conditioning were the worst I’ve ever experienced, which made my stay much less comfortable."
United States
Carlos
The price is ฿6,745
฿8,065 total
includes taxes & fees
8 Sept - 9 Sept
Montauk Oceanside Suites
Luxury Villa, Patio | Living area

18. Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking
2.0 star property
Bryn Mawr
2.0 out of 10, (1 review)
The price is ฿19,330
฿26,548 total
includes taxes & fees
20 Aug - 21 Aug
Luxury 5 BR Home Free Parking
Luxury House | Living area

19. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is ฿7,434
฿13,241 total
includes taxes & fees
25 Aug - 26 Aug
Spacious 3BR Luxe Escape near NYC
Villa, Garden View | Living area

20. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is ฿7,434
฿13,426 total
includes taxes & fees
31 Aug - 1 Sept
Luxury NYC Home Game Room Free Parking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Coastal Connecticut Hotel Reviews

Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

10/10 Excellent
"Clean room when you need.Staff when you need are there.Shops nearby but better rent a car.Laundry ok."
Massimo 14-night trip
Posted 5 hours ago
Motel 6 New Haven - Branford, CT

Find out more about Coastal Connecticut

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