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

Coastal Connecticut Vacation Rentals

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Our top choices for Coastal Connecticut vacation rentals

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, (195 reviews)
"ABSOLUTELY BEAUTIFUL AND SERENE STAY . WE REALLY ENJOYED OUR STAY !"
United States
Melissa
The price is CA $204
CA $300 total
includes taxes & fees
Oct 29 - Oct 30
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

2. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is CA $252
CA $376 total
includes taxes & fees
Oct 26 - Oct 27
DUNE Fairfield Beach

3. Bright Downtown Studio near Yale & East Rock!

Bright Downtown Studio near Yale & East Rock!
Downtown New Haven
9.2 out of 10, Wonderful, (16 reviews)
"Pretty close to Yale campus"
United States
Dongjian
The price is CA $162
CA $355 total
includes taxes & fees
Oct 11 - Oct 12
Bright Downtown Studio near Yale & East Rock!

4. Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (37 reviews)
"Great place. Had everything we needed and was very clean."
United States
Niki B.
The price is CA $121
CA $168 total
includes taxes & fees
Oct 28 - Oct 29
Cozy One Bedroom Apartment Centrally Located in Southbury

5. Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min
Downtown Bridgeport
9.6 out of 10, Exceptional, (13 reviews)
"Perfect option for a quick visit, Would stay again!"
United States
Destiny
The price is CA $156
CA $273 total
includes taxes & fees
Oct 5 - Oct 6
Stylish Sheek Loft Dwntwn, Amphitheater, Park, Metro North, Ferry All 2-10min

6. Spacious 2 Bedroom apartment close to Yale Bowl

Spacious 2 Bedroom apartment close to Yale Bowl
West New Haven
9.6 out of 10, Exceptional, (79 reviews)
"Clean, thoughtful, safe. Great stay"
United States
Daniel S.
The price is CA $162
CA $299 total
includes taxes & fees
Oct 5 - Oct 6
Spacious 2 Bedroom apartment close to Yale Bowl

7. The Sicilian

The Sicilian
West New Haven
9.2 out of 10, Wonderful, (16 reviews)
"It was the perfect day and very convenient for our trip for our son’s graduation. Thank you for being so receptive and helpful."
United States
Michele B.
The price is CA $139
CA $344 total
includes taxes & fees
Oct 5 - Oct 6
The Sicilian

8. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.2 out of 10, Wonderful, (15 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is CA $167
CA $412 total
includes taxes & fees
Oct 19 - Oct 20
Once the old Schools house now a newly furnished Apartment

9. Yale Casa Verde Studio

Yale Casa Verde Studio
Dwight
9.2 out of 10, Wonderful, (15 reviews)
"We had a very nice stay here! The hosts were lovely and very communicative, and they were able to help us with any problems we had very quickly."
United States
Luke
The price is CA $113
CA $265 total
includes taxes & fees
Oct 19 - Oct 20
Yale Casa Verde Studio

10. Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
9.4 out of 10, Exceptional, (6 reviews)
"It was amazing , clean and awesome and good time"
United States
Michael
The price is CA $156
CA $349 total
includes taxes & fees
Oct 1 - Oct 2
Private Apartment in Southbury 103

11. Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.6 out of 10, Exceptional, (27 reviews)
"Very accurate description of listing - host was very responsive. Would stay again!"
United States
Anonymous traveller
The price is CA $179
CA $559 total
includes taxes & fees
Oct 1 - Oct 2
Luxury Designer 2 bedroom+office/3bed vacation home.

12. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
The price is CA $167
CA $412 total
includes taxes & fees
Oct 19 - Oct 20
All New 1BR with tons of Charm

13. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
The price is CA $170
CA $326 total
includes taxes & fees
Oct 26 - Oct 27
1-bedroom cottage with Grove Beach 🏖️ access.

14. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (37 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
The price is CA $177
CA $363 total
includes taxes & fees
Oct 19 - Oct 20
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

15. Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (9 reviews)
"We had a great stay. Comfortable home with a large living room. Beds were great. "
United States
Jason V.
The price is CA $213
CA $506 total
includes taxes & fees
Oct 6 - Oct 7
Angelica’s safe haven @ west haven

16. Stocked home close to Yale, in Heart of New Haven

Stocked home close to Yale, in Heart of New Haven
Mill River
9.0 out of 10, Wonderful, (29 reviews)
"Great value very close to university. "
United States
Lawrence
The price is CA $211
CA $362 total
includes taxes & fees
Oct 5 - Oct 6
Stocked home close to Yale, in Heart of New Haven

17. Bear Retreat - 2-bedroom house in Waterbury

Bear Retreat - 2-bedroom house in Waterbury
Waterbury
10.0 out of 10, Exceptional, (9 reviews)
"Perfect, spacious area. Super clean. Communication was great. Would definitely book here again."
United States
Radha
The price is CA $166
CA $465 total
includes taxes & fees
Oct 8 - Oct 9
Bear Retreat - 2-bedroom house in Waterbury

18. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (11 reviews)
"Great little quiet home away from home. Tom and Stacy and all the cute animals were very friendly and welcoming. Perfect place to relax after a busy day of activity."
United States
Angela A.
The price is CA $149
CA $200 total
includes taxes & fees
Oct 7 - Oct 8
The Tiny Cottage & Mini Farm

19. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is CA $167
CA $415 total
includes taxes & fees
Oct 5 - Oct 6
Newly Remodeled 1-BR Close to Everything yet Very Private

20. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (43 reviews)
"Very convenient location with good parking"
United States
Anonymous traveller
The price is CA $197
CA $343 total
includes taxes & fees
Oct 26 - Oct 27
Walk To Goodspeed Opera House!
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

Find out more about Coastal Connecticut

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Coastal Connecticut. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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