Baltimore Holiday Rentals, Chester: Private House Rentals

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Our top choices for Baltimore hotels

A large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.

An outdoor event space with tables set for dining, surrounded by a covered area with a transparent roof.

A rustic dining area with wooden beams, tables, chairs, and a fireplace.

A living room with a sofa, ottoman, armchair, and a television on a stand.

1. The Inn at Weathersfield

Perkinsville

Dorrie

฿7,618

฿9,540 total

includes taxes & fees

5 Nov - 6 Nov

A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.

A spacious lobby with a fireplace, leather seating, and a chandelier.

A sign for Castle Hill Spa surrounded by lush greenery and a well-maintained lawn.

2. Pointe at Castle Hill Resort

Cavendish

Cristian

฿5,408

฿6,165 total

includes taxes & fees

25 Oct - 26 Oct

A large stone building with a steep roof, surrounded by dense forest and hills.

A spacious living room with a fireplace, red sofas, a wooden coffee table, and a television.

A hotel room with a bed, a nightstand, a lamp, a door, and a view into another room with a couch and a window.

A spacious living room with a fireplace, comfortable seating, and a large window providing natural light.

3. Castle Hill Resort And Spa

Cavendish

Brandon

฿9,042

฿9,856 total

includes taxes & fees

5 Nov - 6 Nov

A cozy living room with a stone fireplace, a leather sofa set, a wooden coffee table, and a patterned rug.

A variety of dishes including a steak, muffins, and a dessert with fruit.

A two-story building with a central entrance, a balcony with railings, and a sign indicating it is a lodging and fine dining establishment.

A bedroom with a bed, a bedside table, a lamp, a mirror, a dresser, a window, and a ceiling fan.

4. Fullerton Inn

Chester Depot

Tim

฿4,353

฿4,745 total

includes taxes & fees

10 Nov - 11 Nov

A bay window seating area with a round table, a potted plant, and a garland with pine cones and lights.

A stone facade with a wooden door, steps leading up to a porch, and a small white chair outside.

A restaurant with a stone wall bar area, wooden tables, and chairs.

A room with a red sofa, armchairs, a coffee table, and a fireplace. There is a window with a view of trees and a chandelier.

5. The Hartness House

Springfield

Zhenchun

฿6,805

฿7,486 total

includes taxes & fees

19 Nov - 20 Nov

A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

An indoor swimming pool with clear water, lounge chairs, and a stone fireplace.

A hotel room with a bed, a sitting area, a bathroom with a bathtub, and a large mirror.

A hotel room with a bed, a sofa, a coffee table, a desk, and a TV.

6. Best Western Springfield Hotel

Springfield

Bryan

฿5,111

฿5,622 total

includes taxes & fees

2 Nov - 3 Nov

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

A living room with two sofas, a fireplace, and a wooden floor.

A conference room with a long wooden table, multiple chairs, and a large window providing natural light.

A white house with a porch, wooden chairs, and an American flag.

7. Stone Hearth Inn and Eatery

Chester

John

฿7,049

฿7,683 total

includes taxes & fees

16 Nov - 17 Nov

A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

A modern hotel room with a bed, a seating area with a chair and a small table, a TV mounted on the wall, and a window with curtains.

A bar area with a hexagonal tiled wall, a wooden planter with greenery, a metal tray with cookies, and a menu board on the wall.

8. Main and Mountain Bar & Motel

Ludlow

David

฿8,829

฿9,712 total

includes taxes & fees

16 Nov - 17 Nov

A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.

A golf course with rolling hills, trees, and a distant mountain range.

A hot tub with a tiled interior and a window in the background.

A balcony with a stone wall and wooden railing overlooking a grassy area with a building in the background.

9. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

Adriana

฿6,232

฿7,572 total

includes taxes & fees

18 Nov - 19 Nov

A multi-story hotel with a central courtyard and a reflective water feature.

A bar area with stools, a counter, and a large window offering a view of a snowy landscape.

A spacious living area with a staircase, patterned sofas, a coffee table, and a decorative wall piece.

A living room with a fireplace, a sofa, a coffee table, and a television.

10. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

Sara

฿4,666

฿5,641 total

includes taxes & fees

5 Nov - 6 Nov

A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.

A wooden interior with a pool, benches, and a clock.

A metal bucket with a spoon, two wine glasses, and a checkered cloth on a brick ledge by a pool.

A cozy room with a large bed, a fireplace, and a brick wall.

11. The Common Man Inn & Restaurant

Claremont

Anna

฿4,373

฿4,745 total

includes taxes & fees

1 Nov - 2 Nov

A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

A well-maintained lawn with a central garden area, a brick building, and a view of a forested hill.

A cozy room with a wooden bench, a chair, and a sofa. There are large windows with wooden frames and a chandelier hanging from the ceiling.

A bedroom with a large window, a bed, a chair, and a lamp.

12. The Jackson

West Woodstock

Ava

฿4,157

฿4,573 total

includes taxes & fees

16 Nov - 17 Nov

A large estate with a main building surrounded by a well-maintained lawn and a river.

A two-story house with a balcony, surrounded by lush greenery and a pond.

A spacious living room with a large American flag, a fireplace, and a chandelier.

A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.

13. On The River Inn

West Woodstock

SARAH

฿5,507

฿6,732 total

includes taxes & fees

15 Nov - 16 Nov

A spacious living area with a fireplace, a dining area, and a kitchen.

A green wooden house with a sloped roof and a front porch.

A modern kitchen with white cabinets, a central island with bar stools, a stainless steel refrigerator, and pendant lighting.

A hotel room with two beds, a mural of mountains, a window with a view of trees, and a cable car on the wall.

14. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Ludlow

฿46,168

฿72,262 total

includes taxes & fees

24 Oct - 25 Oct

A hotel room with two beds, a wooden headboard, bedside lamps, and a window with curtains.

A reception desk with a check-in counter, a framed picture above it, and a potted plant to the right.

A building with a 'Public Welcome' sign, a vending machine, and a hanging flower basket.

A hotel room with a desk, chair, television, refrigerator, and a dresser.

15. Claremont Motor Lodge

Claremont

Marguerite

฿4,032

฿4,375 total

includes taxes & fees

5 Nov - 6 Nov

A two-story house with a front porch, a central entrance, and a garden with various plants and flowers.

A bar area with wooden bar stools, hanging light fixtures, and a bartender at the counter.

A brick oven pizza station with a chef preparing dough.

A two-story brick house with a white porch and a small garden in front.

16. Kedron Valley Inn

South Woodstock

Maytee

฿7,832

฿8,616 total

includes taxes & fees

4 Nov - 5 Nov

A large two-story house with a front porch and a well-maintained lawn.

A rustic interior with wooden beams, a fireplace, and a chandelier.

A spacious room with high ceilings, wooden beams, large windows, and tables and chairs arranged for dining.

A cozy interior with a bar area, wooden furniture, and a Christmas tree.

17. The Landgrove

Londonderry

Alan

฿6,398

฿6,974 total

includes taxes & fees

2 Nov - 3 Nov

An aerial view of a residential area with houses, a river, and surrounding hills.

A fire pit surrounded by Adirondack chairs on a paved patio with a view of a lake and trees.

A two-story building with a central entrance, a small porch, and a driveway leading to a parking area.

A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

18. The Shire Woodstock

Woodstock

John

฿4,039

฿4,798 total

includes taxes & fees

22 Nov - 23 Nov

A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

A row of cabins with a river in the foreground, surrounded by trees and a snowy landscape.

A hotel room with two beds, a desk, and a chair. The room has a wooden floor and red walls with framed pictures.

A modern kitchen with a wooden dining table, stainless steel appliances, and a view of the outdoors through the window.

19. Sleep Woodstock Motel

Woodstock

Dave

฿2,873

฿4,454 total

includes taxes & fees

19 Nov - 20 Nov

A room with a checkered floor, a bench, and a fireplace.

A rustic dining area with wooden beams, a chandelier, and a kitchen in the background.

A large, white building with a symmetrical facade, multiple windows, and a central entrance with steps.

A spacious living room with a grand chandelier, large windows, and a comfortable seating area.

20. Woodstock Inn & Resort

Woodstock

Ann

฿12,452

฿15,182 total

includes taxes & fees

16 Nov - 17 Nov

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Top Baltimore Hotel Reviews

Sleep Woodstock Motel

10/10 Excellent

"The room was so cute and decorated with flair!! The beds were comfortable."

Lincoln Inn & Gallery

10/10 Excellent

"."

The Landgrove

10/10 Excellent

"It was certainly a remote property and if you want to get away from it all then this is the place!"

The Jackson

10/10 Excellent

"Quaint and elegant property. Thebinsite restaurant was great. Enjoyed our 1 night stay here at The Jackson."

Claremont Motor Lodge

10/10 Excellent

"This is my go-to overnight for annual 4x4 weekend. Deciding to stay her is a no brainer. Very clean, professional."

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"Beautiful resort with amazing beds! Very comfortable."

The Hartness House

10/10 Excellent

"pretty"

Fullerton Inn

10/10 Excellent

"Stayed there 7yrs.ago and had another great experience this time, Cloe our waitress was excellent and made our dining alot of fun."

More cheap stays in Baltimore

The Upper Pass Lodge at Magic Mountain

420 Magic Mountain Access Road Londonderry VT

฿3,146

฿3,603 total

25 Oct - 26 Oct

includes taxes & fees

Royal Inn Claremont

24 Sullivan St Claremont NH

฿3,780

฿4,101 total

5 Nov - 6 Nov

includes taxes & fees

6.8/10 (362 reviews)

Claremont Motor Lodge

16 Beauregard St Claremont NH

฿4,032

฿4,375 total

5 Nov - 6 Nov

includes taxes & fees

8.8/10 Excellent! (600 reviews)

Sleep Woodstock Motel

4324 West Woodstock Road Woodstock VT

฿2,873

฿4,454 total

19 Nov - 20 Nov

includes taxes & fees

9.6/10 Exceptional! (642 reviews)

Fullerton Inn

40 The Common Chester VT

฿4,353

฿4,745 total

10 Nov - 11 Nov

includes taxes & fees

8.2/10 Very good! (461 reviews)

Best Western Springfield Hotel

818 Charlestown Rd Springfield VT

฿5,111

฿5,622 total

2 Nov - 3 Nov

includes taxes & fees

Frequently asked questions

What's the best place for a stay in Baltimore?

Woodstock Inn & Resort, located 18.4 mi (29.5 km) from the heart of Baltimore, is a top choice for your stay, based on our traveller data. Other good choices for your trip to the area are The Jackson and Pointe at Castle Hill Resort. See all available top hotels, or vacation rentals in Baltimore.

If I need to cancel my hotel reservation in Baltimore, will I receive a refund?

Yes! The majority of hotel bookings are fully refundable provided that you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If your reservation is non-refundable, you might still have the option to cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Baltimore.

What is staying in Baltimore like?

Those travelling to Baltimore will definitely enjoy the sights to see and things to do. There are 1429 hotels and other accommodation options in the surrounding area. Find out more about Baltimore.

What is there to see in Baltimore?

Places to visit in the wider area include Fox Run Golf Course, Okemo Mountain Resort and Mount Ascutney. You'll also find Mt Ascutney State Park and Lake Rescue in the area. Take a look at what more there is to see and do in Expedia's Baltimore guide.

What's the seasonal weather like in Baltimore?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Baltimore are January, March, November and February, with each month seeing an average of 35 cm of snowfall.

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Book Hotels in Baltimore on Expedia.com

Find hotels in Baltimore, VT from ฿3,603

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Baltimore

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Baltimore hotels

1. The Inn at Weathersfield

2. Pointe at Castle Hill Resort

3. Castle Hill Resort And Spa

4. Fullerton Inn

5. The Hartness House

6. Best Western Springfield Hotel

7. Stone Hearth Inn and Eatery

8. Main and Mountain Bar & Motel

9. Jackson Gore Village, A Vail Resorts Property

10. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

11. The Common Man Inn & Restaurant

12. The Jackson

13. On The River Inn

14. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

15. Claremont Motor Lodge

16. Kedron Valley Inn

17. The Landgrove

18. The Shire Woodstock

19. Sleep Woodstock Motel

20. Woodstock Inn & Resort

Top Baltimore Hotel Reviews

Sleep Woodstock Motel

Lincoln Inn & Gallery

The Landgrove

The Jackson

Claremont Motor Lodge

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

The Hartness House

Fullerton Inn

More cheap stays in Baltimore

The Upper Pass Lodge at Magic Mountain

Royal Inn Claremont

Claremont Motor Lodge

Sleep Woodstock Motel

Fullerton Inn

Best Western Springfield Hotel

Frequently asked questions

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