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Vacation rentals in Orange

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Top-rated vacation rentals in Orange

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Cottage in Petersham

4.99 out of 5 average rating, 179 reviews

Cider House Cottage

Antique guest cottage on a country farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub.

Cottage in Bernardston

4.88 out of 5 average rating, 307 reviews

Cozy, Quiet Cottage on Country rd 2 mil from I-91

Our quite and comfy home is conveniently located less than 2 miles from I-91, but a 1/4 mile down a country road giving you lots of privacy. The cottage is less than a mile from Crump 'N Fox Golf; 2 miles from Northfield Mount Hermon; 10 minutes from Greenfield & Stoneleigh Burnham; 15 min to Brattleboro, Deerfield Academy, Bement & Eaglebrook; 20 min to UMass, Amherst & Northampton; 30 minutes to Keene NH & Shelburne Falls and 45 min to the Basketball Hall of fame in Springfield & Mt Snow VT.

Rental unit in Conway

4.95 out of 5 average rating, 139 reviews

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, then known as "Goat Meadow Farm". We hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

Rental unit in Dublin

4.97 out of 5 average rating, 215 reviews

Private Dublin apartment nestled in the woods

Nestled in the quiet woods just north of Mt. Monadnock our cozy one bedroom apartment invites the outdoors in with peeks of the mountain through the trees. Sit out on your private deck and enjoy the view or stroll around the yard and pick a few blueberries in season. We welcome hikers, nature lovers, those visiting friends or family or just wanting to enjoy the area's beautiful scenery and many artistic venues. I like to think of it as a peaceful sanctuary that we'd like to share with you.

Guest suite in Ashburnham

4.98 out of 5 average rating, 436 reviews

The Ginger Bed King Suite

Come for the lovely country setting, the winter beauty, amenities, neighborhood, convenience, privacy, spaciousness, and the comfortable bed. Close to many wonderful hiking/biking paths, rail trails, Wachusett ski area, Jewel Hill, Lake Wampanoag, Kirby area. WI-FI, TV ( Hulu and Netflix), refrigerator, microwave, coffee/tea maker, reading lights, table area, continental breakfast, parking... Good for couples, solo and business travelers. (Key pad for Covid safe entry) Everyone is welcome!

Loft in Greenfield

4.97 out of 5 average rating, 98 reviews

Treehouse Retreat

This loft apartment is on the 3rd and 4th floors of a Victorian mansion. It boasts a dozen skylights and cathedral ceilings, making you feel like you're up in the trees. A jacuzzi tub, full kitchen, and large work tables make this an ideal spot for a relaxing getaway or artist's retreat. Located a couple of blocks from downtown Greenfield. Easy walk to great restaurants, cinema, shops, train station, farmers' market and co-op. 2nd bedroom with king bed and ensuite bath available for fee.

Rental unit in Pelham

4.99 out of 5 average rating, 144 reviews

Pelham 2nd floor Apartment

Second floor newly finished apartment that accommodates 2 guest. Well water and septic. Green by recycling and using salvage materials. Environmentally benign materials used where possible. Solar. Utilities and internet included. Raspberries and blueberries in season. 3.9 miles from UMASS and Amherst Colleges. 5.3 miles from Hampshire College. 11 miles from Mt. Holyoke and 12 miles from Smith College. NO PETS ACCEPTED! Allergy free. Don't hesitate to contact us with questions!

Guesthouse in Westminster

4.98 out of 5 average rating, 358 reviews

Guest House - 4 miles from Wachusett Mt.

Enjoy your stay in this cozy, newly renovated semi-attached in-law unit. It is located close to Route 2, walking distance to the town center, only 4 miles from Mt. Wachusett in a quiet neighborhood. It has 2 parking spaces and a private entrance. This unique space has everything to make you feel at home – including WiFi and Netflix. The kitchen is equipped with a Keurig Coffee Maker, Mini Fridge, and a Microwave. Queen-size bed, fresh towels, body wash are also provided.

Rental unit in Winchester

4.91 out of 5 average rating, 191 reviews

Downtown Loft next to Distillery

Enjoy a lovely weekend getaway in this cute 1 bedroom loft, centrally located in Winchester, NH. Enjoy a tasting at New England Sweetwater Farm & Distillery next door and a pint on us at Outlaw Brewing Company. This cozy loft features a full kitchen, 3/4 bath as well as a bedroom and living/dining room. 20 minutes to Keene, Brattleboro and Chesterfield. Access to Pisgah State Park, the Ahsuelot Rail Trail and Forest Lake. Come see what our beautiful area has to offer!

Cottage in Orange

4.93 out of 5 average rating, 159 reviews

The Lake Cottage: A Sweetwater Stay

Welcome to Mattawa Cove! Originally built as an Ice Fisherman's shack, this tiny house is unapologetically elegant and understated. The private dock can be viewed from the wall of windows in the open living space. Walk to the shore, sit with your feet in the water, swim, fish, or kayak. It’s the ultimate, all-year romantic getaway. With excellent Wi-Fi, you can stay as connected as you'd like to the outside world. 1.5 hours from Boston or Providence. 3.5 hours to NYC.

Tiny home in Orange

4.92 out of 5 average rating, 346 reviews

The Writer's Retreat: A Sweetwater Stay

Located on the shore of Tully Pond, The Writers Retreat is a newly designed 325sqft lake side cottage with breathtaking views of Tully Mountain. This 4-season cottage is built with salvaged barn wood; up-cycled maple floors and custom built furniture and lighting. It's the little sister to The Fishing Cottage. You'll find this intimate home has everything you need to relax, write the next Great American Novel, connect with a lover, or just plain chill.

Guest suite in Fitzwilliam

4.98 out of 5 average rating, 166 reviews

The Great Room in Historic Fitzwilliam

Come relax in the great room! Large space with full bathroom, beautiful picture windows, spacious closet, and use of deck included. Deck includes a cozy fire pit table, gas grill, and a nice view of the beaver pond, great for bird watching! Please don't hesitate to reach out if you are traveling with children and/or pets, we are often able to accommodate on a case by case basis. Please note stairs are required for entry via the deck entrance.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

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Popular amenities for Orange vacation rentals

Free parking on premises

Air conditioning

Stay near Orange's top sights

Jumptown9 locals recommend

Walmart Supercenter8 locals recommend

Honest Weight Artisan Beer8 locals recommend

Tea House7 locals recommend

Herrick's Tavern6 locals recommend

Anne's Dairy Drive In5 locals recommend

Other great vacation rentals in Orange

Guesthouse in Wendell

4.93 out of 5 average rating, 29 reviews

Quiet Country Home in Wendell

Farm stay in Warwick

4.97 out of 5 average rating, 62 reviews

Be Still Meadows at Chase Hill Farm - first floor

Guest suite in Guilford

4.97 out of 5 average rating, 126 reviews

Private, Quiet Studio With Mountain Views

Guesthouse in New Ipswich

4.95 out of 5 average rating, 332 reviews

"The Porch" Your cozy home away from home!

Cottage in Warwick

4.99 out of 5 average rating, 83 reviews

Corkscrew: Lakeside Cozy Cottage in Warwick, MA

Cottage in Warwick

4.94 out of 5 average rating, 31 reviews

By Still Waters Cottage

Cottage in Orange

4.99 out of 5 average rating, 78 reviews

Lake House with view of mountain

Cabin in Athol

5 out of 5 average rating, 31 reviews

Panoramic Sunroom | Soaking Tub | Modern Cabin

Quick stats about vacation rentals in Orange

Total rentals
30 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
2.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace

Frequently Asked Questions

Do house rentals in Orange have wifi?
Absolutely! We offer over 10 house rentals with wifi in Orange. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Orange have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Orange. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Orange have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Orange. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Orange?
Four-legged friends are welcome in Orange. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Orange?
Yes! Work meets play with ease at over 10 vacation rentals in Orange featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Orange?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in house rentals in Orange?
Experience the best of Orange with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Orange have free parking?
Absolutely! We offer over 10 house rentals with free parking in Orange. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore