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

Our top choices for Orange vacation rentals

A house with a staircase leading to a porch, surrounded by snow and string lights.

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
$254 nightly
The price is $284
Sep 28 - Sep 29
Total with taxes and fees
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

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.
$197 nightly
The price is $220
Oct 12 - Oct 13
Total with taxes and fees
Lovely 2nd Floor Apartment
A grassy outdoor area with a hammock, chairs, and a stone wall.

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
$175 nightly
The price is $185
Sep 23 - Sep 24
Total with taxes and fees
Little House Inn - Private Home - Secluded - Ware - 2 bedroom, sleeps 6
A staircase with a wooden handrail and white steps, leading to a landing with a wooden table and a clock.

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.
$367 nightly
The price is $388
Sep 23 - Sep 24
Total with taxes and fees
Enjoy your stay in an antique home in an antique toy museum!
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

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.
$273 nightly
The price is $296
Sep 23 - Sep 24
Total with taxes and fees
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A blue house with a porch, a wooden bench, and a door.

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.
$240 nightly
The price is $268
Oct 5 - Oct 6
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
An outdoor grill area with a stone patio, a red building wall, and a view of a lake.

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.
$361 nightly
The price is $392
Sep 23 - Sep 24
Total with taxes and fees
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A cabin with a dock extending into a calm river, surrounded by snow-covered trees and a clear sky.

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.
$303 nightly
The price is $329
Sep 23 - Sep 24
Total with taxes and fees
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

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.
$581 nightly
The price is $649
Sep 23 - Sep 24
Total with taxes and fees
Spacious 5BR w/ Hot Tub & Games
A wooden gazebo with a metal roof, surrounded by a brick patio with outdoor seating.

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.
$297 nightly
The price is $314
Oct 18 - Oct 19
Total with taxes and fees
Serene 1-bedroom suite on 75 acre horse property
A lakeside park with picnic tables and a concrete walkway.

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

2 private mountain RV pads for rent. Full hook ups
Winchester
$75 nightly
The price is $81
Sep 23 - Sep 24
Total with taxes and fees
2 private mountain RV pads for rent. Full hook ups
A bedroom with a bed, dresser, mirror, and a television.

12. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
$546 nightly
The price is $610
Sep 23 - Sep 24
Total with taxes and fees
Penthouse overlooking downtown Amherst!
A house by a lake with a dock and a boat.

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.
$241 nightly
The price is $262
Sep 23 - Sep 24
Total with taxes and fees
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A modern two-story house with large windows and a balcony.

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.
$570 nightly
The price is $637
Sep 28 - Sep 29
Total with taxes and fees
Cozy Valley View Post & Beam Villa!
A cabin with a covered porch, large windows, and snow-covered ground.

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.
$280 nightly
The price is $304
Oct 18 - Oct 19
Total with taxes and fees
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A modern interior with large windows, a wooden ceiling, and a cozy seating 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.
$464 nightly
The price is $519
Sep 24 - Sep 25
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
A living room with a black leather sofa, a wooden coffee table, and a fireplace with a blue accent.

17. A Cozy Condo Near Horse Farm + Mount Sugarloaf

A Cozy Condo Near Horse Farm + Mount Sugarloaf
Sunderland
$406 nightly
The price is $454
Sep 29 - Sep 30
Total with taxes and fees
A Cozy Condo Near Horse Farm + Mount Sugarloaf
A rustic cabin with a covered porch, a small shed, and outdoor seating.

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
$145 nightly
The price is $157
Sep 23 - Sep 24
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

19. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$335 nightly
The price is $340
Sep 23 - Sep 24
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

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.
$442 nightly
The price is $480
Sep 23 - Sep 24
Total with taxes and fees
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

Hotel UMass

Hotel UMass

10/10 Excellent
"Everything was great I just would not count on any type of special breakfast it’s just fruit and danish type of breakfast. Free coffee on the way out was great!"
Steven 1-night trip
Posted less than an hour ago
Hotel UMass

Find out more about Orange

Everything you need to know about Orange vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Orange vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Orange vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Orange vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Orange. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Orange in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $157 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Orange rentals

At Expedia, we put the best Orange vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Orange rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Orange vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Orange. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.