Chester Holiday Rentals, Vermont: Private House Rentals

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Go beyond your typical stay in Chester

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Our top choices for Chester hotels

Iron/ironing board (on request), free WiFi, bed sheets

1. Fullerton Inn

Chester Depot

Kirsty

3.636.518 ₫

3.963.805 ₫ total

includes taxes & fees

31 Aug - 1 Sept

Luxury Room, Mountain View | Blackout curtains, free WiFi, individually decorated

2. Stone Hearth Inn and Eatery

Chester

Olena

5.455.136 ₫

5.946.098 ₫ total

includes taxes & fees

1 Sept - 2 Sept

Suite, 1 King Bed, Non Smoking, Jetted Tub | Laptop workspace, iron/ironing board, rollaway beds, free WiFi

Suite, 1 King Bed, Accessible, Refrigerator & Microwave (with Sofabed) | Laptop workspace, iron/ironing board, rollaway beds, free WiFi

3. Best Western Springfield Hotel

Springfield

Gerry

4.207.549 ₫

4.628.303 ₫ total

includes taxes & fees

3 Sept - 4 Sept

4. The Common Man Inn & Restaurant

Claremont

Denis

3.508.324 ₫

3.806.571 ₫ total

includes taxes & fees

7 Sept - 8 Sept

River View | Iron/ironing board (on request), free WiFi, bed sheets

5. Harvest Barn Inn

Bellows Falls

Michael

4.549.048 ₫

4.958.463 ₫ total

includes taxes & fees

31 Aug - 1 Sept

6. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

3.139.440 ₫

3.406.292 ₫ total

includes taxes & fees

3 Sept - 4 Sept

Family Room, 1 Double Bed, 1 King Bed, 1 Twin Bed | Premium bedding, free WiFi, individually decorated

7. Bromley View Inn

Bondville

William

2.000.347 ₫

2.200.225 ₫ total

includes taxes & fees

27 Aug - 28 Aug

Exclusive Double Room | Living area | 32-inch flat-screen TV with digital channels, TV, streaming services

8. The Hartness House

Springfield

Dan

4.636.430 ₫

5.100.074 ₫ total

includes taxes & fees

26 Aug - 27 Aug

Sauna, aromatherapy, hot stone massages, deep-tissue massages

Suite, 1 King Bed, Sofa Bed & Full Kitchen | Private kitchen | Coffee/tea maker

9. Pointe at Castle Hill Resort

Cavendish

David

3.979.240 ₫

4.536.334 ₫ total

includes taxes & fees

26 Aug - 27 Aug

Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave | Premium bedding, in-room safe, iron/ironing board, free WiFi

10. Claremont Motor Lodge

Claremont

Sergio

2.872.760 ₫

3.116.944 ₫ total

includes taxes & fees

31 Aug - 1 Sept

Suite, 1 King Bed with Sofa bed, Non Smoking | Desk, blackout curtains, iron/ironing board, free WiFi

11. Comfort Inn & Suites Brattleboro I-91

Brattleboro

Morgan

3.091.040 ₫

3.400.144 ₫ total

includes taxes & fees

7 Sept - 8 Sept

Exclusive Suite, Multiple Beds, Kitchenette, Mountain View | 1 bedroom, desk, iron/ironing board (on request), free WiFi

12. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

2.395.393 ₫

2.658.886 ₫ total

includes taxes & fees

1 Sept - 2 Sept

Villa, 1 Bedroom | Iron/ironing board, bed sheets

13. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

Gene

3.636.518 ₫

4.395.477 ₫ total

includes taxes & fees

26 Aug - 27 Aug

Standard Room, 2 Queen Beds, Refrigerator & Microwave | Desk, iron/ironing board, rollaway beds, free WiFi

14. The Putney Inn

Putney

JANE

2.849.042 ₫

3.133.946 ₫ total

includes taxes & fees

1 Sept - 2 Sept

Room, 1 King Bed, Non Smoking | Blackout curtains, free WiFi, bed sheets

15. Black Mountain Inn

Brattleboro

Robert

3.113.278 ₫

3.424.606 ₫ total

includes taxes & fees

27 Aug - 28 Aug

16. Hampton Inn and Suites Manchester

Manchester Center

Patricia

4.054.587 ₫

4.460.046 ₫ total

includes taxes & fees

2 Sept - 3 Sept

Suite, 1 King Bed with Sofa bed | Desk, blackout curtains, iron/ironing board, free WiFi

17. Colonial Motel

Brattleboro

James

2.149.731 ₫

2.364.703 ₫ total

includes taxes & fees

26 Aug - 27 Aug

Standard Room, 2 Double Beds | Desk, blackout curtains, iron/ironing board, free WiFi

Combined shower/bathtub, hair dryer, towels

Desk, blackout curtains, iron/ironing board, free WiFi

18. Royal Inn Claremont

Claremont

Eva

2.825.496 ₫

3.065.663 ₫ total

includes taxes & fees

26 Aug - 27 Aug

19. Hampton Inn Brattleboro

Brattleboro

Timothy

2.957.352 ₫

3.253.087 ₫ total

includes taxes & fees

8 Sept - 9 Sept

Premium bedding, desk, laptop workspace, blackout curtains

20. Best Western Plus Keene Hotel

Keene

Karen

3.898.138 ₫

4.229.611 ₫ total

includes taxes & fees

6 Sept - 7 Sept

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Where to stay in Chester

Find the best Chester areas for the activities you enjoy most.Learn more about Chester

Chester Depot

A forest with autumn foliage in various colors.

Chester Depot

If you're spending some time in Chester Depot, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.

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Stay near popular Chester attractions

Bonnie's Bundles Dolls

7.6/10 (4 reviews)

This historic Vermont studio showcased handcrafted cloth dolls with embroidered faces and calico clothing. Visitors treasured personal interactions with artist Bonnie Watters and stories behind her creations.

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DaVallia Art & Accents

10.0/10 (2 reviews)

This Vermont art haven showcases fine local art and handcrafted furniture in thoughtfully designed spaces. Browse both the Art Boutique and 39 North Gallery to experience indoor exhibits and outdoor sculpture gardens.

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Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

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A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top Chester Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"It was good!"

The Shire Woodstock

8/10 Good

"It was a nice and cozy place to stay and experience Woodstock VT."

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent

"👍"

Latchis Hotel

8/10 Good

"The room was very clean and the staff was amazing but the proximity of the hotel makes it hard to sleep in the morning. It’s at a very busy intersection, and the train comes through and blasts its horn early in the morning.It is a great place to stay, but if you want to sleep in, it’s not the right place for you."

Colonial Motel

8/10 Good

"X"

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good

"The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus."

Hampton Inn Brattleboro

10/10 Excellent

"Staff were extremely friendly. The whole place was clean. Hit tub was really a whirlpool..movement but no bubbles. So nice and warm though. Great stay!!"

The Equinox Golf Resort & Spa

10/10 Excellent

"We loved this hotel, really nice amenities, great rooms. I wish we had planned less activities and spent more time at the hotel. If you want to stay in the hotel, plan to spend a day in the hotel. Breakfast ends at 11 and bar closes at around 10 depending on crowd."

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"The front desk staff were friendly and engaged, the room was clean. That’s all we needed."

More cheap stays in Chester