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Compare 306 Vacation Homes in Chester with updated reviews, rates, and availability.

Cozy Westbrook Vacation Rental - Walk to Beach!

10.0 out of 10, Exceptional, (11)
"Stayed at this house for a weekend after Christmas. It was great! Perfect location and easy to get everywhere! Would love to stay again."
Cozy Westbrook Vacation Rental - Walk to Beach!

Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

10.0 out of 10, Exceptional, (22)
"This house that we stayed at was amazing. Room for everyone, plenty of entertainment, and the neighborhood was quiet. Mary was also very responsive & available for any questions we had. Will definitely stay here again! 5"
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>

Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College

9.6 out of 10, Exceptional, (44)
"We loved being next door to Ocean Beach."
Ocean Beach Park Lawrence M.Hosp MitchellCollege Coast Guard Academy CT College

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property

Spectacular home with an amazing river view

9.6 out of 10, Exceptional, (72)
"Had a weekend getaway with a group of friends. The house was amazing, the pictures don't do justice. Host was great with communication. Would definitely book again in the future."
Spectacular home with an amazing river view

Walk to the beach at Black Point, Niantic, Ct.

9.8 out of 10, Exceptional, (86)
"Wonderful space in a beautiful quiet neighborhood near ocean and cute small town if Niantic"
Walk to the beach at Black Point, Niantic, Ct.

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

10.0 out of 10, Exceptional, (9)
"My friends and I have stayed twice now at this house and have had the best time both times! It has everything we could need in the house and we can’t wait to be back again!"
The price is AED 2,204
AED 3,133 total
includes taxes & fees
26 Jan - 27 Jan
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+

10.0 out of 10, Exceptional, (10)
"This may very well be the nicest house we have ever stayed in! It was spacious, clean and well stocked. It was so nice not to have to bring our own linens! We were pleasantly surprised with a hot tub. Thank you for a great stay!"
Expansive Beautiful Ranch with Pool and hot tub. Close to Beach Sleeps 20+

The beach is waiting.

10.0 out of 10, Exceptional, (25)
"Susan's place was perfect for my family to visit the neighborhood where I grew up! It was clean, comfortable and had everything we needed. It's also a few steps from the beach and the amenities GNB has to offer."
The beach is waiting.

Enjoy a taste of New England in Historic Guilford Ct

10.0 out of 10, Exceptional, (9)
"Wonderful property combining original details with modern amenities. Well located near the town green and shops. We would definitely stay here again."
Enjoy a taste of New England in Historic Guilford Ct

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.

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (8)
"Host worked with me due to larger dog. Very accurate instructions and all amenities were very good. Will stay here again"
Ranch style living at its best with country garden & patio!

Waterford Manitock Spring Water Residence with handicap accessible home

10.0 out of 10, Exceptional, (4)
"I recently had the pleasure of staying at the Manitock Spring Water Residence in Waterford, Connecticut, and it was a delightful experience. The home is thoughtfully designed with handicap accessibility, ensuring comfort for all guests. Its location is ideal, with Lawrence + Memorial Hospital, Flanders Plaza Shopping Center, Hempstead Houses and Mystic all within a short drive. The open-concept design of the dining room and kitchen creates an airy and inviting atmosphere. The host was attentive...
Waterford Manitock Spring Water Residence with handicap accessible home

Charming 3-bedroom ranch in soothing Montville, 1 minute from Mohegan Sun.

2.0 star property
9.8 out of 10, Exceptional, (6)
"Everything was great. Perfect location. Pleased with the stay."
The price is AED 1,102
AED 1,899 total
includes taxes & fees
9 Feb - 10 Feb
Charming 3-bedroom ranch in soothing Montville, 1 minute from Mohegan Sun.

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (2)
"We came to stay at Gilbert’s for a quick ski weekend at Powder Ridge. Gilbert was incredibly gracious and accommodating. He was very easy to communicate with, and really went out of his way to make us feel at home. The location is a little loud at night/early morning, as it is very close to a main road. But the property itself was exactly as described. Clean, comfortable, and very welcoming. "
The price is AED 360
AED 677 total
includes taxes & fees
12 Feb - 13 Feb
Family Stays: Middletown, CT

Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos

10.0 out of 10, Exceptional, (33)
"Spacious, full stocked, amenity filled home with enough room for family members to gather and/or spread out.The game room is perfect for all ages with a variety of choices for your competitive play. Grocery/liquor store and Gillette Castle State Park are minutes away.Beautiful area. "
Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (26)
"When my hometown sib couldn't host, we rented here and had our family Thanksgiving! It was great!"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

10.0 out of 10, Exceptional, (24)
"The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings."
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

10.0 out of 10, Exceptional, (87)
"My husband and I stayed at this property with our family members over the New Year's holiday (Dec. 27th to Jan. 3rd). We had the most amazing time. The house has such wonderful space (huge family room/dining area with an super-sized propane fireplace, large kitchen, and family members got their pick of the numerous bedrooms and bathrooms). Its central location to so many other CT towns makes the property even more special and of course, the immense acreage with the plentiful fields and...
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

Storybook Cottage

10.0 out of 10, Exceptional, (1)
"Very charming property, accurate description per listing. Very clean and overall a great stay."
Storybook Cottage
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

Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premises

10.0 out of 10, Exceptional, (11)
"This was a lovely place to stay after a day at the spa. Super clean, updated, easy check in. The only thing we didnt like was the foam mattress on the bed. You would sink into a hole, making it hard to move. But nothing that would make me not stay here again. 5/5 would recommend "
The price is AED 459
AED 951 total
includes taxes & fees
27 Jan - 28 Jan
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premises

Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

10.0 out of 10, Exceptional, (31)
"The perfect place to relax and get ready for a night out after an amazing day at the spa. Wish we had more time to enjoy the fireplace and rhe balcony. Nice open space wirh plenty of room and very well equipped, comfortable. We loved it!"
The price is AED 643
AED 1,259 total
includes taxes & fees
4 Feb - 5 Feb
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (24)
"We loved our trip. The cottage is beautifully done and the views incredible. We appreciated the hospitality extended by our host (and Nico the dog!) and enjoyed exploring the nearby woodland. Our kids are already asking if we can go back and visit again. "
Private Guest House w/ Deck + Spectacular Views!
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.