Chester Vacation Rentals
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49 rentals in Chester.
Charming Chester Retreat- Near Village Center
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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![Stunning Artisan Waterfall Escape [Walk to Downtown], vacation rental in Chester](https://dynamic-media.tacdn.com/media/vr-ha-splice-j/10/1a/47/e4.jpg?w=800&h=-1)
![Stunning Artisan Waterfall Escape [Walk to Downtown], vacation rental in Chester](https://dynamic-media.tacdn.com/media/vr-ha-splice-j/12/bd/c5/d9.jpg?w=800&h=-1)
![Stunning Artisan Waterfall Escape [Walk to Downtown], vacation rental in Chester](https://dynamic-media.tacdn.com/media/vr-ha-splice-j/10/01/ef/b9.jpg?w=800&h=-1)
Stunning Artisan Waterfall Escape [Walk to Downtown]
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Millhouse Downtown Chester
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The following properties within 32 kms of Chester match all your filters:
⚓Capt Nathaniel Clarke Historic HomesteadWeddings�Reunions❤Magnificent Yard�
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Charming 2 Bedroom Guest House in Essex, CT
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Downtown Essex Apartment - Steps to River!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Winter at the Haddam House
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Patchogue River Retreat, 8 minute walk to West Beach
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Stunning, peaceful and private home
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious living on a bucolic alpaca farm
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Essex Home w/ Large Yard Near Downtown!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cheerful, private cottage in Essex village.
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Bucolic Carriage House In Beautiful Lyme CT
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cozy Yacht with Marina Views
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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PRIVATE LAND ....OPEN SPACE 30 ACRES with POND, Very Basic
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 4
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Available July 21-28, 2023
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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East Haddam Country Loft......
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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New inside and Out! Beautiful Lake Front Home
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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NEW!!! On VBRO! CT Shoreline Beach Diamond!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Private waterfront home in Historic in Essex CT
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The perfect New England getaway only a 10 minute walk to downtown!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Storybook Cottage
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Renovated Barn, Sidewalk Stroll into Essex Village & Marina
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxurious country get away at Flat Rock Farm with alpaca as your neighbors
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Newly Renovated Private Quiet Cape 1/2 mile from the beach
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Cottage with Roger’s Lake views and access.
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Essex Village home within walking distance to downtown.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Historic Sanctuary on the Pond
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Beautiful/Relaxing Lakehouse-Sleeps 8-Large Deck with Furniture-Family Friendly
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly Constructed 3 Bedroom, 2 Bath Home on 12.5 Acres, Water Access and Views
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Spectacular Home with Deep Water Dock
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stroll to beach at charming, historical, rustic home w/expansive yard & pool.
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern 70s Architectural Marvel - ★★★ Water and Hillside Views
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Beach front property steps from Long Island Sound!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Home with Endless Charm | Relax, Entertain, Enjoy!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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River and Sunset views!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Near Hartford - 2 Hours from NYC
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Private beautiful setting, Lyme's best kept secret, Swim, Boat, Fish, Hike
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Fantastic pool home in park-like setting on Connecticut Shore
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Exquisite Beach Villa In Ground pool and Spacious Bermuda room! 2 living Rooms!
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Peace Barn in the heart of the CT River Valley
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded Family escape w/ pool & jacuzzi
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Luxury Enchanted Estate w/ Expansive Views & Private Pool, Hot Tub, Tennis Court
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Mansion on the hill
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Private resort style pool, hot tub, cabana bar and fun game room
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Magnificent Victorian Mansion on Bashan Lake Connecticut DIRECT LAKEFRONT
Holiday Rental House
9 bedrooms
4 bathrooms
Sleeps 21
Match: Sleeps
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Lovely, cozy Cottage on a non working farm in a rural town. Quiet and private.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Showing results 1-49 of 49
Frequently Asked Questions about Chester
- Yes, here are some popular vacation rentals in Chester that have a pool:
- Charming Chester Retreat- Near Village Center
- Stunning Artisan Waterfall Escape [Walk to Downtown]
- The Millhouse Downtown Chester
- Yes, here are some popular vacation rentals in Chester that have internet access:
- Charming Chester Retreat- Near Village Center
- Stunning Artisan Waterfall Escape [Walk to Downtown]
- The Millhouse Downtown Chester
- Some of the most popular kid friendly rentals in Chester are:
- Charming Chester Retreat- Near Village Center
- Stunning Artisan Waterfall Escape [Walk to Downtown]
- The Millhouse Downtown Chester