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Chester Vacation Rentals

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Vacation Rentals in Chester

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (6)
"I loved this escape from reality. This was a very quiet romantic getaway for Valentine’s Day. The place was very clean and had everything we needed from a fully equipped small kitchen to everything outdoors we would need for a campfire and making s’mores. I loved this place and can’t wait to come back for another romantic getaway."
The price is CA $193
CA $222 total
includes taxes & fees
Mar 19 - Mar 20
Postcard Cabins Machimoodus

Regency Inn & Suites

The price is CA $109
CA $178 total
includes taxes & fees
Mar 19 - Mar 20
Regency Inn & Suites

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

9.6 out of 10, Exceptional, (80)
"Enjoyed a long weekend here. Nice and clean, kitchen equipped with all upgraded utensils and pans, very comfy beds and plenty of space for all. Will definitely come back."
Waterfront House with picture-perfect views from all 3 levels.

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

10.0 out of 10, Exceptional, (32)
"Everything was absolutely perfect! The place is adorable inside and out and so close to Mohegan. It was ideal for a mother/daughter trip to see Billy Joel. Thank you! "
The price is CA $250
CA $490 total
includes taxes & fees
Mar 19 - Mar 20
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

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

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

⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

9.8 out of 10, Exceptional, (127)
"We loved our stay!"
The price is CA $430
CA $867 total
includes taxes & fees
Mar 25 - Mar 26
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

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

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 CA $317
CA $663 total
includes taxes & fees
Mar 19 - Mar 20
Cozy Coastal Cottage.

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (25)
"Meetings with friends who were staying at Mohegan Sun which was 20 minutes away. Pretty views, comfortable property. Would definitely return "
Private Guest House w/ Deck + Spectacular Views!

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

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 CA $119
CA $165 total
includes taxes & fees
Mar 19 - Mar 20
Regency Inn and Suites - Handicapped Non Smoking with Mobilty Access

Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

10.0 out of 10, Exceptional, (59)
"Our family ranged in ages from 13 to 96. We were 12 people for a couple days and then 10. We all had a marvelous time and my mom just can’t stop talking about how beautiful the view and the antique furniture was. It was difficult for that many people only having two bathrooms, but we made it work. We did run out of hot water so we learned to scatter showers when possible. The view is amazing and the location was wonderful for us. I can’t say enough, how accommodating our hostess was. We told her...
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

9.4 out of 10, Exceptional, (33)
"Our second stay at the cottage. We spent a long weekend and the weather cooperated. The house is quite quirky, but has a really pleasant feel at home vibe. Beds were very comfortable. Kitchen could use some updates, but was sufficient. (still need a new can opener) The porch overlooking the Sound is magical. Nice neighborhood. If you have one...bring a golf cart! Lots of golf carts about. Host is always pleasant, communicating through Vrbo. We hope to return again. Thank you Khalig Family...
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

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

9.8 out of 10, Exceptional, (17)
"Easy to find. Quiet community. So quiet, two female deer were walking through the parking lot. Saw ducks and plenty of other wildlife. Hit the hot tub!!! Very clean inside, had all our needs for cooking. Overall excellent trip. Will be back in the summer."
The price is CA $141
CA $319 total
includes taxes & fees
Mar 20 - Mar 21
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premises

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (107)
"Cute place, very clean"
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

9.0 out of 10, Wonderful, (22)
"Spent a weekend in this cottage while attending an event for my daughter. Very cozy and comfortable. Host was great, with excellent communication. Renovations are taking place in adjacent units, however it did not impact my stay. Highly recommend. "
The price is CA $106
CA $216 total
includes taxes & fees
Mar 22 - Mar 23
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

Spacious Oceanview Villa (Sleeps 22)

10.0 out of 10, Exceptional, (34)
"Absolutely loved staying here. Katie was super helpful and my group had an amazing time. The house is plenty big for big groups. While my group was supposed to be 16, we only had 8 but it felt even more special! Everyone had their own rooms & thoroughly enjoyed their time. Thank you for being an incredible host, Katie! "
Spacious Oceanview Villa (Sleeps 22)

Historical New England coastal holiday home-2 min. from Ocean Beach

10.0 out of 10, Exceptional, (34)
"Everything was amazing! The house, the owners and time with friends. The house was wonderfully appointed, the beds were comfortable and the water was in sight from the front porch. Would DEFINITELY stay here again! "
Historical New England coastal holiday home-2 min. from Ocean Beach

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
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 types of properties in Chester you may be interested in

Motel 6 New Haven - Branford, CT

2.0 star property
6.8 out of 10, (1001)
"Very nice and staff friendly "
The price is CA $97
CA $113 total
includes taxes & fees
Mar 23 - Mar 24
Motel 6 New Haven - Branford, CT

Mohegan Sun

4.5 star property
9.2 out of 10, Wonderful, (1783)
"The pools in each tower were game changers. Not inexpensive, but a lovely stay!"
The price is CA $313
CA $396 total
includes taxes & fees
Apr 2 - Apr 3
Mohegan Sun

Hyatt Place Uncasville - Casino Area

3.0 star property
9.2 out of 10, Wonderful, (2364)
"Nice staff. Delicious breakfast."
The price is CA $152
CA $174 total
includes taxes & fees
Apr 7 - Apr 8
Hyatt Place Uncasville - Casino Area
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.

Frequently asked questions

Are there vacation rentals in Chester?

Yes, we offer vacation rentals close to well known sights in Chester, or you can go with a more secluded option if you'd like a relaxing place to stay. Chester is known for its waterfront and parks. Make sure you have time to check out the theaters while you're in the area.

What are some of the best vacation rentals in Chester?

Waterfront House with picture-perfect views from all 3 levels.: This vacation home near Chester is located on the beach and has a furnished patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Chester?

Expedia has 3 vacation rentals for your stay in Chester.

What’s there to see and do in Chester?

Connecticut River and Connecticut Valley Railroad State Park Trail are a couple of scenic spots to enjoy the outdoors, whereas Norma Terris Theater is one of the cultural attractions. Chester Creek Marina and Gillette Castle State Park are a couple of places you'll find in the larger area.

What’s a vacation rental in Chester like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Chester. Vacation rentals offer extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family trip or a small group gathering.