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Chester Holiday Rentals

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Holiday Rentals in Chester

Property grounds
Private Guest House w/ Deck + Spectacular Views!
10.0 out of 10, Exceptional, (11)
"Our floors were being refinished so we needed a place to stay for a week with our dog. The cottage was perfect for our needs, with plenty of space to walk our dog."
Private Guest House w/ Deck + Spectacular Views!
Indoor pool, a heated pool
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
10.0 out of 10, Exceptional, (13)
"We just returned and loved our time at the villa! We chose to stay here for 2 nights of concerts at Mohegan sun and could not have been happier! The property is clean, comfortable and has everythign you could need. The snacks and water were a welcomed treat! Taylor was so accomodating and we hope to return one day!"
The price is NZ$524
per night
29 May - 30 May
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Aerial view
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, (7)
"Adorable cottage with full kitchen, luxurious bathroom and comfiest beds!! Cutest cul de sac with friendly neighbors"
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
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Interior
70 Year old cottage on 2.8 acres, stunning views and sunsets
70 Year old cottage on 2.8 acres, stunning views and sunsets
Property grounds
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
9.4 out of 10, Exceptional, (3)
"This VRBO was very Comfortable. Old Rustic House thats Been Upgraded with Modern Accomodations. We felt Very Relaxed here. We cooked Dinner /Breakfast . and enjoyed some Livation. Sitting area outside was perfect. . and we slept well.. . The only thing we were surprised about was the On Street Parking for unloading. And the Stairs at the Entrance.. Not Handicap Accesibble. But, in the end.. We were very happy. And will stay again. No Problem"
The price is NZ$446
per night
4 Jun - 5 Jun
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
Property grounds
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (110)
"I stayed at this amazing studio cottage with my girlfriend for 2 nights for her birthday. Our hosts, Liz and Adam were simply amazing. They allowed us an early check in and a late check out. Liz even brought out bicycles for us to use to tour around the neighborhood and ride along the shore line. Because it was my girlfriends birthday (or maybe they just do this), they had Prosecco and Orange Juice plus beer and cheese and other snacks for us when we arrived. The cottage is adorable, perfect...
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Beach nearby, sun-loungers, beach towels
Beach House
9.8 out of 10, Exceptional, (43)
"My daughter graduated from coast guard academy so we were staying for several days. The cottage is located in black point in Niantic. So close to the ocean. The cottage was adorably decorated, and very comfortable. Plenty of beds to accommodate a bigger group. Slept very well in comfortable bed. The owner had left some bagels and muffins for us as well. Small but nice kitchen with plenty of room for a family to sit at larger table. My favorite is proximity to water and the daily multiple walks....
Beach House
Property grounds
Waterfront Home with a View
9.6 out of 10, Exceptional, (90)
"Peaceful environment, beautiful views, comfort galore. The property lights at night time were a pleasant surprise. Just a few "oh,nooo" comments: laundry was left in the dryer and the washer had some gunk on the inside - the rubber seal when you open it. The dishwasher had spots of mildew in the utensils spot. The wall hook for the curtain in the bedroom broke on the first night - it was barely in the wall. The Keurig was a bonus, 2 touchlanmps in the bedroom with charging ports, large comfy...
The price is NZ$472
per night
16 Jun - 17 Jun
Waterfront Home with a View
Interior
Shalom Cottage with private beach rights.
9.4 out of 10, Exceptional, (8)
"Has everything you need for 2, for a Summer stay. (The portable heater didn't keep up with the December evenings)."
Shalom Cottage with private beach rights.
Beach nearby, sun-loungers, beach towels
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (88)
"Positive experience, great location, and cozy accommodations for a centrally located family weekend."
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Pool
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
10.0 out of 10, Exceptional, (10)
"We had a big group with all different ages. Everybody enjoyed their stay. The home was clean, comfortable, and very thoughtfully decorated. The pool table, poker table and Pac-Man kept us all entertained during out time there. Hosts were friendly and responsive."
Ocean Beach Fun! 3 bedroomsDog ok with fee and signing of pet agreement!<br>
3 bedrooms, desk, iron/ironing board, WiFi
The Bay Cottage · Rocky Neck Park, Beach & Niantic
10.0 out of 10, Exceptional, (5)
"I booked this for a sister weekend. It was perfect for what we needed. It appears that the house was built to be a summer getaway, so it is pretty basic and no frills and comes with all the creaks and quicks of an older house. The living room is perfect for hanging out and the four chairs make it easy to rearrange to suit your needs. The kitchen is nicely stocked with everything you would need to stay with a family and the dining room is spacious enough to easily accommodate everyone staying...
The price is NZ$752
per night
29 May - 30 May
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Exterior
"Salt 'n' Lyme" - Walk to everything !
9.4 out of 10, Exceptional, (20)
"This cottage is so adorable and just a short walk to the beach and a local convenience store. This makes it easy to park the car and just walk to get coffee and such. We stayed in October so not much open this time of year, but we were in the area for a family wedding so not much time to hang out anyway. This was the first time I've rented on Vrbo, so I wasn't sure what to expect as have read a lot about obnoxious owners with tons of rules, but Brett is super-chill with only a couple of things...
"Salt 'n' Lyme" - Walk to everything !
Fridge, microwave, stovetop, dishwasher
Remodeled Farmhouse in Waterford Near 2 Beaches!
10.0 out of 10, Exceptional, (60)
"Great stay, convenient location, very charming house with everything we needed."
Remodeled Farmhouse in Waterford Near 2 Beaches!
Fridge, microwave, oven, stovetop
Spacious, beautiful home. 5-min walk to beach. 1 min to Water's Edge Resort!
10.0 out of 10, Exceptional, (41)
"This home was immaculately clean, well decorated and well equipped. It had everything you need including toiletries (soap, shampoo, conditioner, etc). I would definitely recommend it."
Spacious, beautiful home. 5-min walk to beach. 1 min to Water's Edge Resort!
Smart TV, fireplace
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, (6)
"House was very nice. Location is great. Easy walk to beach and convenient to Westbrook center."
Patchogue River Retreat, 8 minute walk to West Beach
Property grounds
Beautiful 4BR Beach House with Private Beach Access.
10.0 out of 10, Exceptional, (65)
"Visited family back in CT and this was the perfect place to stay. Kind of like a Tardis, it was bigger on the inside! Thank you!"
Beautiful 4BR Beach House with Private Beach Access.
Beach nearby, beach towels
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
9.8 out of 10, Exceptional, (38)
"Great place. Cozy cottage!"
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
Fridge, microwave, oven, dishwasher
Close to Mystic, Stonington, Westerly. Room for everyone. 3 mins to Ocean Beach.
9.8 out of 10, Exceptional, (21)
"This was a great place for us to have the whole family for a graduation from the USCGA. Plenty of space for everyone and a great outdoor area that we used a lot since the weather was beautiful. The hosts were very responsive. We would stay again."
Close to Mystic, Stonington, Westerly. Room for everyone. 3 mins to Ocean Beach.
View from property
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
10.0 out of 10, Exceptional, (71)
"Beautiful inn in a wonderful setting. The farm is beautiful and the lake is nearby. Delicious dinner was prepared for us."
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
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See all available properties in Chester
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.

Other types of properties in Chester you may be interested in

Interior entrance
Mohegan Sun
4.5 star property
9.2 out of 10, Wonderful, (1596)
"This place was amazing! I can literally live in there and never have to leave. It was an amazing stay, everything is very clean and there is something there for amy one and everyone. "
The price is NZ$372
per night
30 May - 31 May
Mohegan Sun
Exterior
Hyatt Place Uncasville - Casino Area
3.0 star property
9.0 out of 10, Wonderful, (2060)
"Awesome place to stay. Large very clean rooms. Highly recommend. "
The price is NZ$242
per night
3 Jun - 4 Jun
Hyatt Place Uncasville - Casino Area
Exterior
Red Roof Inn Meriden
2.0 star property
7.6 out of 10, Good, (1000)
"Very clean and updated! Surprised there was no fridge in the room though!"
The price is NZ$183
per night
23 Jun - 24 Jun
Red Roof Inn Meriden
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chester holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chester. 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 Chester. Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your 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 holiday 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 Chester short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its waterfront and parks. Make sure you have time to check out the theatres while you're in the area.

What are some of the best holiday rentals that Chester has to offer?

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA: This holiday home rental outside of Chester is equipped with a garden, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Chester?

Expedia has 3 holiday 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. While here, Cockaponset State Forest and Chester Creek Marina are other places worth a visit.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.

Recent reviews of Chester properties
Expedia verified reviews