Orange Holiday Rentals, Massachusetts: Private House Rentals

A calm lake surrounded by autumn-colored trees and a hilly landscape.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Orange

Pet friendly

Apartment

Pool

Family friendly

Waterpark

Condo

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Orange hotels

A bedroom with a geometric-patterned headboard, a bed with a textured white duvet, two pillows, a bedside table with a clock, and a potted plant.

A grassy area with picnic tables and a clock tower.

A room with a round table and two leather chairs, a window with curtains, and a view of a parking lot outside.

A large, single-story building with a central entrance and a covered walkway.

1. Windmill Motel Restaurant

Bernardston

Donna

3.318.084 ₫

3.706.300 ₫ total

includes taxes & fees

11 Oct - 12 Oct

An indoor swimming pool with clear water, surrounded by windows with a view of trees.

A breakfast area with a sign reading 'HAPPY BREAKFAST STARTS HERE.'

A hotel lobby with a fireplace, seating area, and large windows.

A hotel with a large entrance, a sign reading 'Hampton Inn & Suites,' and a parking lot.

2. Hampton Inn & Suites Greenfield

Greenfield

Robert

4.985.534 ₫

5.568.842 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A two-story house with a red door, green shutters, and a snow-covered front yard.

A kitchenette with a refrigerator, a coffee station, and a fruit basket.

A group of women in formal attire standing in a garden with a house in the background.

A golf course with a brick pathway, wooden boxes, and a tee box.

3. Centennial House

Northfield

Alan

4.643.455 ₫

4.908.132 ₫ total

includes taxes & fees

13 Oct - 14 Oct

A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.

A brick building with a red awning and a sign that reads "The Inn."

A conference table set for a meeting with chairs and folded red napkins.

A conference room with a long table, six chairs, a projector screen, and a brick wall.

4. The Inn At Crumpin Fox

Bernardston

Heather

2.910.600 ₫

3.251.076 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with a large TV screen displaying the hotel name, red chairs, wooden shelves, and a clock on the wall.

A modern building with a grid-like facade, multiple balconies, and a spacious courtyard with geometric sculptures.

A hotel room with two beds, a dining table with a plate of food, a glass of water, and a bottle of wine.

A registration desk with a sign above it, a receptionist, and several people standing in line.

5. Hotel UMass

Amherst

Darrell

2.838.417 ₫

3.206.635 ₫ total

includes taxes & fees

26 Oct - 27 Oct

An indoor swimming pool with clear signage, a lifeguard chair, and a no diving warning.

6. Comfort Inn & Suites Hadley - Amherst

Hadley

John

3.105.675 ₫

3.469.039 ₫ total

includes taxes & fees

4 Nov - 5 Nov

A large, historic building with a prominent tower and a well-lit entrance labeled "Bollywood".

A modern living room with a sofa, armchairs, a coffee table, and a wine rack.

A spacious outdoor seating area with a fire feature, white brick walls, and multiple windows with shutters.

A long dining table set with white tableware, flanked by windows and a skylight.

7. Inn on Boltwood

Amherst

pam

5.332.219 ₫

5.956.089 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A gaming area with arcade machines, a seating area with tables and chairs, and large windows providing natural light.

A hotel room with a television displaying a football game, a desk with a lamp, a microwave, and a refrigerator.

A hotel room with two beds, a desk, a chair, a TV, and a mirror.

A Red Roof Plus hotel with a modern facade, a parking lot, and a landscaped entrance area.

8. Red Roof Inn PLUS+ South Deerfield – Amherst

South Deerfield

Edward

2.310.370 ₫

2.580.684 ₫ total

includes taxes & fees

1 Nov - 2 Nov

An outdoor seating area with wicker furniture, a fire pit, and decorative lamps.

A dining table set with multiple wine glasses, a centerpiece with flowers, and candles.

A conference room with two Dell computers, a large autumn-themed painting, and two wall-mounted lamps.

A spacious lobby with a central seating area, a reception desk, and a television screen.

9. Courtyard by Marriott Hadley Amherst

Hadley

Yuki

3.702.283 ₫

4.135.450 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A bar area with a high ceiling and stained glass windows, bar stools, and a checkered floor.

A spacious lobby with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

A covered outdoor area with a wooden deck, white railings, and string lights.

A gazebo with a white fence and a blue roof, surrounded by a well-maintained lawn, with a brick building in the background.

10. Best Western Plus Keene Hotel

Keene

Ruddy

3.662.182 ₫

3.973.467 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A neatly arranged hotel room with a bed, a chair, a desk, and two framed pictures on the wall.

A wooden sign with 'RESTAURANT RECEPTION ENTRANCE' and an arrow pointing right.

A hotel room with a bed, a chair, a lamp, and a window with curtains.

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

11. Deerfield Inn

Deerfield

Deborah

7.195.003 ₫

9.266.773 ₫ total

includes taxes & fees

13 Oct - 14 Oct

A grand lobby with a staircase, a piano, comfortable seating, and large windows.

A formal dining room with round tables, dark wooden chairs, and white tablecloths.

A brick building with a steeple, arched windows, and flags.

A pool area with lounge chairs and potted plants.

12. The Colonial Hotel

Gardner

John Timothy

3.724.274 ₫

4.160.217 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel reception area with two counters labeled 'Choice Hotels' and 'Ascend Hotel Collection'. There are vending machines and a refrigerator with beverages.

A hotel room with a bed, a desk, a chair, a wooden door, and a window.

An indoor swimming pool with clear blue water, a lifebuoy, and a few lounge chairs.

A modern fitness center with cardio machines, weightlifting equipment, and a large mirror.

13. Keene Elm City Hotel, an Ascend Collection Hotel

Keene

Angelo

3.078.768 ₫

3.340.463 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

A hotel suite shop with shelves stocked with snacks and sundries, a refrigerated display case, and a sign indicating 24-hour availability.

A modern hotel with a clear entrance, a parking area, and a sign indicating a 11' clearance.

An indoor swimming pool with lounge chairs and a sign indicating no lifeguard on duty and no diving.

14. Hampton Inn & Suites Keene

Keene

Rebecca

3.892.442 ₫

4.223.300 ₫ total

includes taxes & fees

10 Nov - 11 Nov

A room with a bed, a sofa, a coffee table, and a television.

A living room with a round coffee table, a sofa, and a wall art piece.

A large brick building with a prominent entrance and a covered porch area.

A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a television mounted on the wall.

15. Black Walnut Inn

North Amherst

Kristen

4.544.415 ₫

5.076.112 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A modern hotel lobby with a stone wall, a fireplace, a bar area, and seating arrangements.

A modern kitchen with stainless steel appliances, a microwave, and a dishwasher. There is a dining area with a table and chairs.

An outdoor seating area with chairs and tables, a covered patio with string lights, and potted plants.

A modern lounge area with a stone wall, a fireplace, a sofa, and two blue armchairs.

16. Homewood Suites by Hilton Hadley Amherst

Hadley

Rebecca

4.009.643 ₫

4.478.771 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A living room with a brick wall, two armchairs, a sofa, a coffee table, and a patterned rug.

A bar area with a fireplace, seating, and a TV.

A hotel room with a brick wall, a large bed with white bedding, a flat-screen TV, and a desk with a lamp.

17. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Caroline

4.486.205 ₫

4.867.532 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A view of a red building by a waterway through a window.

A bar area with wooden stools, a long counter, and potted plants.

A yellow multi-story building with a water feature in front.

A wooden porch with a sign reading "OLD MILL" above a double door.

18. Old Mill Inn

Hatfield

John

4.643.455 ₫

5.186.739 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A bar area with a dark tiled backsplash, multiple stools, and a variety of bottles and glasses on the counter.

A hotel room with two beds, a desk, an orange chair, and a view of buildings through the window.

A modern hotel lobby with a central bar area, multiple seating arrangements, and a reception desk.

An indoor swimming pool with clear water, a glass railing, and a seating area with tables and chairs.

19. Courtyard by Marriott Keene Downtown

Keene

Deborah

4.891.102 ₫

5.306.846 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A dock extending into a lake with a grassy area in the foreground and trees in the background.

A building with a large balcony overlooking a body of water, a bridge in the foreground, and trees with autumn foliage.

A spacious living room with a large window, a patterned rug, and multiple seating options including a sofa and armchairs.

A spacious bedroom with a large bed, a desk, and a television.

20. Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

Jason

3.936.425 ₫

4.271.021 ₫ total

includes taxes & fees

8 Nov - 9 Nov

View all properties

Hotels recommended for families in Orange

Hampton Inn & Suites Greenfield

Greenfield

4.985.534 ₫

5.568.842 ₫ total

includes taxes & fees

1 Nov - 2 Nov

Windmill Motel Restaurant

Bernardston

3.318.084 ₫

3.706.300 ₫ total

includes taxes & fees

11 Oct - 12 Oct

Hotel UMass

Amherst

2.838.417 ₫

3.206.635 ₫ total

includes taxes & fees

26 Oct - 27 Oct

The Inn At Crumpin Fox

Bernardston

2.910.600 ₫

3.251.076 ₫ total

includes taxes & fees

1 Nov - 2 Nov

Comfort Inn & Suites Hadley - Amherst

Hadley

3.105.675 ₫

3.469.039 ₫ total

includes taxes & fees

4 Nov - 5 Nov

Best Western Plus Keene Hotel

Keene

3.662.182 ₫

3.973.467 ₫ total

includes taxes & fees

1 Nov - 2 Nov

Inn on Boltwood

Amherst

5.332.219 ₫

5.956.089 ₫ total

includes taxes & fees

1 Nov - 2 Nov

Courtyard by Marriott Hadley Amherst

Hadley

3.702.283 ₫

4.135.450 ₫ total

includes taxes & fees

26 Oct - 27 Oct

Save an average of 15% on thousands of hotels when you're signed in

Learn more about Orange

Outdoor enthusiasts flock to this quaint New England town for hiking trails and kayaking on the Millers River. History buffs can explore the Orange Historical Society's museum, while foodies shouldn't miss sampling local maple syrup at nearby farms.

See all hotels in Orange

Top Orange Hotel Reviews

Latchis Hotel

8/10 Good

"Love the old-fashioned, art, deco, charm, and having the turntables and old records in the room… And having the movie theater attached…. I think this is a work in progress. The carpeting is really old in the rooms and there were laundry bags left out for the laundry to pick up all day… And because they don’t staff from 10 PM to 9 AM on a Saturday I had to literally fill the water jug for the Keurig coffee from my tub… Could you not. But the staff was great and it’s a cool looking old hotel… The windows need to be clean so I could actually see the mountains out of my room… And be able to close the outside windows. If you want old World charm give it a try… But I’m hoping or not for private he has taken this over. I’ll put some more cash into it because it’s worth it."

Hotel UMass

10/10 Excellent

"Very convenient and included parking"

The Colonial Hotel

10/10 Excellent

"Nice hotel. Floors creeked. Need was comfortable."

Gardner Inn

10/10 Excellent

"Top match budget hotel"

Colonial Motel

8/10 Good

"very convenient and cost was good, as we stay in Brattleboro as our daughter and granddaughter live in Turners Falls Mass. and its only a half hour drive to visit with them."

The Inn At Crumpin Fox

8/10 Good

"Lovely setting."

Black Walnut Inn

10/10 Excellent

"The way B&B's used to be with innkeepers who liked to interact with the vacationers; with a home cooked breakfast(s) that was near perfect (not boiled eggs and cold cereal); and with accommodations that were clean and comfortable. we will be back!"