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

Orange Vacation Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Orange vacation rentals

Exterior

1. Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
10.0 out of 10, Exceptional, (12 reviews)
"Nice place"
United States
Tom
The price is AED 826
AED 1,042 total
includes taxes & fees
28 Sep - 29 Sep
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Interior

2. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (66 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is AED 474
AED 808 total
includes taxes & fees
12 Oct - 13 Oct
Lovely 2nd Floor Apartment
Property grounds

3. Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6

Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Ware
9.8 out of 10, Exceptional, (26 reviews)
"Nice place to stay a lot of family activities on the premises short distance to shopping and attractions"
United States
Andrew
The price is AED 568
AED 678 total
includes taxes & fees
23 Sep - 24 Sep
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
Interior

4. Enjoy your stay in an antique home in an antique toy museum!

Enjoy your stay in an antique home in an antique toy museum!
Winchendon
9.4 out of 10, Exceptional, (9 reviews)
"What a fun stay! Great communication with the property manager Don, cute town, lots of American history to be discovered, fun stay. 10/10 highly recommend!!!"
United States
Katja Z.
The price is AED 1,194
AED 1,425 total
includes taxes & fees
23 Sep - 24 Sep
Enjoy your stay in an antique home in an antique toy museum!
Private kitchen

5. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
Fitzwilliam
10.0 out of 10, Exceptional, (1 review)
"This place was really beautifully appointed and thoughtfully stocked. Kitchen stock was great.Lots of coffees, teas, bottled water…all very thoughtful touches. Comfy beds. Beautiful little home. Pond was really nice. Convenient to Monandock. Really loved it. Lots of appreciation for the hosts."
United States
Len S.
The price is AED 876
AED 1,086 total
includes taxes & fees
23 Sep - 24 Sep
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
Exterior detail

6. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.6 out of 10, Exceptional, (9 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is AED 407
AED 983 total
includes taxes & fees
5 Oct - 6 Oct
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Terrace/patio

7. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Rindge
10.0 out of 10, Exceptional, (25 reviews)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
The price is AED 716
AED 1,439 total
includes taxes & fees
23 Sep - 24 Sep
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Exterior

8. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
9.8 out of 10, Exceptional, (26 reviews)
"Awesome few days away great place and surroundings. Jim is always there for you ."
United States
David S.
The price is AED 809
AED 1,268 total
includes taxes & fees
27 Sep - 28 Sep
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Coffee/tea maker, fridge, microwave, oven

9. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
The price is AED 1,055
AED 2,384 total
includes taxes & fees
23 Sep - 24 Sep
Spacious 5BR w/ Hot Tub & Games
Outdoor dining

10. Serene 1-bedroom suite on 75 acre horse property

Serene 1-bedroom suite on 75 acre horse property
Belchertown
10.0 out of 10, Exceptional, (38 reviews)
"Not your average stay! This place is super cool!!"
United States
Wayne B.
The price is AED 691
AED 1,153 total
includes taxes & fees
18 Oct - 19 Oct
Serene 1-bedroom suite on 75 acre horse property
Outdoor dining

11. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is AED 202
AED 299 total
includes taxes & fees
23 Sep - 24 Sep
2 private mountain RV pads for rent. Full hook ups
Internet, bed sheets

12. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
The price is AED 1,377
AED 2,544 total
includes taxes & fees
4 Oct - 5 Oct
Penthouse overlooking downtown Amherst!
Exterior

13. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (13 reviews)
"Amazing place. We really enjoyed our brief stay. Great host. "
United States
Gary S.
The price is AED 644
AED 1,009 total
includes taxes & fees
23 Sep - 24 Sep
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Property grounds

14. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (12 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is AED 1,837
AED 2,339 total
includes taxes & fees
28 Sep - 29 Sep
Cozy Valley View Post & Beam Villa!
Exterior

15. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
8.0 out of 10, Very good, (5 reviews)
"Hit the jackpot at this stay .Awesome area with many things to keep busy outside ,hiking all around ,lake for all kind of activities .Jim was a great host filled us in on activities in the area and was a message away for any help u may need .I will be back ."
United States
David S.
The price is AED 702
AED 1,133 total
includes taxes & fees
28 Sep - 29 Sep
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Living area

16. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 reviews)
"The glass part of the house is stunning! We wanted to spend all of our time there, and wished that we could enjoy the view from the kitchen and bedroom too. We opted to sleep on the fold-out bed in the glass room instead of in the below-ground bedroom. It was a nice experience!"
United States
Chris O.
The price is AED 796
AED 1,908 total
includes taxes & fees
24 Sep - 25 Sep
Stunning Glass House nestled in the Vermont wilderness!
TV

17. A Cozy Condo Near Horse Farm + Mount Sugarloaf

A Cozy Condo Near Horse Farm + Mount Sugarloaf
Sunderland
The price is AED 1,006
AED 1,932 total
includes taxes & fees
4 Oct - 5 Oct
A Cozy Condo Near Horse Farm + Mount Sugarloaf
Terrace/patio

18. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (19 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is AED 331
AED 578 total
includes taxes & fees
23 Sep - 24 Sep
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Terrace/patio

19. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is AED 1,010
AED 1,192 total
includes taxes & fees
1 Oct - 2 Oct
Vikings Villages Resort - Double Bed Room
Coffee/tea maker, fridge, microwave, oven

20. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (4 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is AED 705
AED 1,761 total
includes taxes & fees
23 Sep - 24 Sep
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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.
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Top Orange Hotel Reviews

The Inn At Crumpin Fox

The Inn At Crumpin Fox

10/10 Excellent
"Amazing would stay again -"
Cole 1-night trip
Posted 2 hours ago
The Inn At Crumpin Fox

Frequently asked questions

Can I find a vacation rental in Orange?

Yes, we give you a choice of vacation rentals near the most popular points of interest in Orange, or you can go with a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals in Orange?

The Jelly Mill-A Peaceful River Retreat: This vacation home rental outside of Orange is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Orange?

Choose from 3 Expedia vacation rentals in Orange for a memorable vacation.

What can I see and do in Orange?

Explore the area and family-friendly sights such as North Common Meadow, or get out into nature at a spot like Millers River. Fish Brook Wildlife Management Area and Northfield Mountain Recreation Center are a couple of places you'll find in the larger area.

What are vacation rentals like in Orange?

Vacation rentals are private accommodations you can stay in for a couple days or more in Orange. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a small group gathering.