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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 401 Vacation Homes in Chester with updated reviews, rates, and availability.

Regency Inn & Suites
1 bedroom, iron/ironing board, WiFi, bed sheets

Regency Inn & Suites

The price is AED 279
AED 458 total
includes taxes & fees
30 Mar - 31 Mar
Regency Inn & Suites
Waterfront House with picture-perfect views from all 3 levels.
Interior

Waterfront House with picture-perfect views from all 3 levels.

9.8 out of 10, Exceptional, (81)
"It was a very nice stay. Sound of the ocean was calming. We would go back. "
Waterfront House with picture-perfect views from all 3 levels.
The Dollhouse is conveniently located. Mystic, Beaches, parks, casinos, shopping
Fridge, microwave, oven, stovetop

The Dollhouse is conveniently located. Mystic, Beaches, parks, casinos, shopping

10.0 out of 10, Exceptional, (11)
"We had a wonderful stay at the Dollhouse. Nick was so accommodating. When we arrived, there was a nice note from Nick and some treats for us. The house was extremely clean and very comfortable. We absolutely loved it and will definitely be back!"
The price is AED 698
AED 1,379 total
includes taxes & fees
20 Apr - 21 Apr
The Dollhouse is conveniently located. Mystic, Beaches, parks, casinos, shopping
Cozy Coastal Cottage.
Fridge, microwave, oven, stovetop

Cozy Coastal Cottage.

10.0 out of 10, Exceptional, (3)
"What a beautiful remodeled house. Cozy and very quiet neighborhood, close to restaurants. "
The price is AED 815
AED 1,704 total
includes taxes & fees
7 Apr - 8 Apr
Cozy Coastal Cottage.
Large Charming Historic House close to Beaches
Fridge, microwave, oven, dishwasher

Large Charming Historic House close to Beaches

9.6 out of 10, Exceptional, (23)
"This was the BEST decision for our family. The house was very cozy, old charm feel with some modern updates. The downstairs bathroom had a Spa vibe. We loved the 6 bedrooms & spacious kitchen & dining room. Loved how close it was to food & entertainment. The walk to the beach was only 10 minutes & very safe. We are use to blinds and/or shades, so just having light curtains for the windows was"
Large Charming Historic House close to Beaches
Cozy Westbrook Vacation Rental - Walk to Beach!
Aerial view

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (13)
"My college friends and I try to get away a few times a year and our latest weekend trip was to Westbrook. I love the Connecticut shore any time of year but off season is my favorite (very affordable hahaha). I was so happy when I walked into this house - sooooo clean, it had everything we needed in the kitchen, comfortable beds, and a very responsive host (thank you Wendy!). Even though it was March we were lucky enough to bundle up and enjoy coffee out on the patio! I can’t say enough about...
Cozy Westbrook Vacation Rental - Walk to Beach!
New Madison beach house - Ocean front- Great views- booking Summer 2025
Exterior

New Madison beach house - Ocean front- Great views- booking Summer 2025

10.0 out of 10, Exceptional, (56)
"Great location "
New Madison beach house - Ocean front- Great views- booking Summer 2025
Waterfront Beach House
Terrace/patio

Waterfront Beach House

9.6 out of 10, Exceptional, (42)
"The property is nicely located on the water and convenient to many attractions. "
Waterfront Beach House
Luxe Lake House in Connecticut
Fridge, microwave, oven, stovetop

Luxe Lake House in Connecticut

10.0 out of 10, Exceptional, (2)
"The house easily accommodated my friends and family for a weekend of relaxation. The place is very spacious with all modern amenities. We especially loved waking up to the gorgeous view of the lake in the back. The views were breathtaking. Would definitely consider going back. "
The price is AED 1,288
AED 3,322 total
includes taxes & fees
30 Mar - 31 Mar
Luxe Lake House in Connecticut
Oceanfront Beach House lay in bed and hear the waves, boats , birds
On the beach, sun loungers, beach towels

Oceanfront Beach House lay in bed and hear the waves, boats , birds

10.0 out of 10, Exceptional, (18)
"Very fun location near the beach. Beach is small but really a nice place to be. House worked well for our family of 4. Sun room was very nice."
Oceanfront Beach House lay in bed and hear the waves, boats , birds
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach nearby, sun loungers, beach towels

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (88)
"Everything was just fine - nothing spectacular but good enough for a short stay. Extremely safe feeling location"
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach House
Beach nearby, sun loungers, beach towels

Beach House

9.8 out of 10, Exceptional, (50)
"Wonderful location. Cozy space we had a wonderful time"
Beach House
OASIS @ OCEAN BEACH PARK: 6 QUEEN BEDS
Interior

OASIS @ OCEAN BEACH PARK: 6 QUEEN BEDS

9.6 out of 10, Exceptional, (23)
"House is in the best location, a mile from Ocean Beach Park, full of privacy with great view. We had very good time and we will definitely come back. It was clean and as described. Minor things needs to be looked at is the AC which is not very powerful but it's not the end of the world and the fact that there is no hood above the range make the house smoky if you want to cook something because you can't open any window. Overall, we are very happy for staying here!!!"
OASIS @ OCEAN BEACH PARK: 6 QUEEN BEDS
Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access
Bar (on property)

Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access

10.0 out of 10, Exceptional, (1)
"It was fine for what we needed it for . Sheets were clean and the tv worked ."
The price is AED 364
AED 492 total
includes taxes & fees
30 Mar - 31 Mar
Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access
Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge
Fridge, microwave, oven, stovetop

Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge

10.0 out of 10, Exceptional, (55)
"Lovely, spacious and clean. We spent our Christmas holiday together with our family and the house was spacious and spotless. We had 5 adults with 2 small children in house. We hosted Christmas dinner for us and local family. Great space. Would love to rent in summer months to utilize outdoor space"
Updated spacious home, huge kitchen, 5 min walk to beach, 1 min to Water's Edge
Vacation Starts Now! Pet friendly, beach fun 5 min away!
Fridge, microwave, oven, stovetop

Vacation Starts Now! Pet friendly, beach fun 5 min away!

10.0 out of 10, Exceptional, (2)
"This house was perfect for a girls' weekend away. The house was pristine, there was plenty of linen, and the kitchen was very well equipped. There were plenty of games, some books, and a tip board for guests to leave each other suggestions and reviews for local attractions. The bottled water, breakfast bars, and popcorn were a great added touch and we loved the "take a bottle, leave a bottle" wine rack! We were 5 adults and a toddler and had plenty of room to spread out (with a much...
Vacation Starts Now! Pet friendly, beach fun 5 min away!
Waterfront Lakehouse in Clinton, CT with Hot Tub!
Outdoor spa tub

Waterfront Lakehouse in Clinton, CT with Hot Tub!

7.0 out of 10, Good, (2)
"My family and I absolutely loved our stay at this home! It was the perfect retreat for us, and we thoroughly enjoyed the hot tub and the breathtaking sunset views, especially while cooking in the beautifully designed kitchen. The kitchen was fully equipped, making it easy to prepare an amazing family dinner. The town of Clinton was absolutely charming, with the friendliest people, and we fell in love with Hammonasset Beach—it’s a must-visit! We’ll definitely be returning in the summer. The...
Waterfront Lakehouse in Clinton, CT with Hot Tub!
Bright and Cheerful Coastal Cottage with Water Access
Smart TV, books, stereo

Bright and Cheerful Coastal Cottage with Water Access

10.0 out of 10, Exceptional, (42)
"This cottage was so lovely and so close to parks and beaches! The neighborhood is quiet and everyone was so welcoming and friendly. Thank you so much to the owners! We had a great time!😊"
Bright and Cheerful Coastal Cottage with Water Access
Grammy's Lake House w/ Private Waterfront Access
Interior

Grammy's Lake House w/ Private Waterfront Access

9.6 out of 10, Exceptional, (11)
"Enjoyable stay, nice property and great views. The home is aged, but the location is amazing! We had a nice weekend excursion to enjoy New England in October. "
Grammy's Lake House w/ Private Waterfront Access
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Beach nearby, sun loungers, beach towels

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (42)
"This property is beautiful and the house is spacious and well equipped for a wonderful stay. The host was attentive and easy to contact when it was necessary. Such a fantastic choice for a stay in a delightful town. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
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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Other property types in Chester

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (7)
"We had a GREAT time here!! Just beautiful scenery all around. The cabin was well equipped with everything we needed essentially. I was quite impressed with how comfortable we actually were. There was a temporary power outage but it didn’t last long and management not only delivered more wood to us but also gave it to us for free as we wanted to spend our time outdoors during the outage. Im super happy to have had this experience and would absolutely be doing it again!! Thank you Postcard...
The price is AED 496
AED 570 total
includes taxes & fees
10 Apr - 11 Apr
Postcard Cabins Machimoodus
Regency Inn & Suites
1 bedroom, iron/ironing board, WiFi, bed sheets

Regency Inn & Suites

The price is AED 279
AED 458 total
includes taxes & fees
30 Mar - 31 Mar
Regency Inn & Suites
Oceanfront Beach House lay in bed and hear the waves, boats , birds
On the beach, sun loungers, beach towels

Oceanfront Beach House lay in bed and hear the waves, boats , birds

10.0 out of 10, Exceptional, (18)
"Very fun location near the beach. Beach is small but really a nice place to be. House worked well for our family of 4. Sun room was very nice."
Oceanfront Beach House lay in bed and hear the waves, boats , birds
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.