Holiday houses in Orange

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Top-rated holiday rentals in Orange

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Guest favourite

Cottage in Petersham

4.99 out of 5 average rating, 148 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.

8 – 15 Nov

$1,754 AUD total

Guest favourite

Cottage in Bernardston

4.88 out of 5 average rating, 285 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.

13 – 20 Dec

$1,551 AUD total

Guest favourite

Apartment in Greenfield

4.96 out of 5 average rating, 267 reviews

Mohawk Trail View/ private apt. no cleaning Fee

Apartment: Entrance, bathroom & driveway are all private. Backyard with gas bbq. Kitchenette has microwave, toaster oven, Keurig coffee maker & sink. 2 TV’s one in living room & bedroom. Netflix, Amazon Prime , HBO & Local programs. High speed internet. Bedroom has Queen bed & desk. Apt. Is 2 min's to Rt. 2 Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes.

24 – 31 July

$1,273 AUD total

Guest favourite

Apartment in Dublin

4.96 out of 5 average rating, 182 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.

28 Sept – 5 Oct

$1,357 AUD total

Superhost

Guest suite in Montague

4.93 out of 5 average rating, 162 reviews

Great Falls Private Suite

Turners Falls is one of 5 villages in the town of Montague. It's a vibrant, diverse area that runs along the Connecticut River. Our lovingly designed guest suite is situated 17 miles from the UMass Amherst Campus, 8.2 miles from Northfield Mount Hermon, 2 miles from downtown Turners Falls and 2.6 miles from downtown Greenfield. If you are looking for a private and bright suite with beautiful natural light and a modern bohemian feel this guest retreat is for you. I look forward to hosting you!

2 – 9 June

$1,200 AUD total

Guest favourite

Guest suite in Ashburnham

4.99 out of 5 average rating, 403 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!

2 – 9 Jan

$1,277 AUD total

Superhost

Guesthouse in Fitzwilliam

4.86 out of 5 average rating, 331 reviews

Tranquil Guest House with Sauna

Are you seeking to escape the city & take a break from hectic schedules & demands? We invite you to embrace life at a relaxed pace surrounded by nature, offering an opportunity to reset your life & cultivate space for stillness & healing. Enjoy the fire pit, walk the trails, forage for treasures & unwind in the wood fired sauna! We've created a place for you to unwind & restore your soul, & detox & recharge your body. For the full retreat ask about day pass to Covey House Healing Center.

23 – 30 Nov

$1,764 AUD total

Guest favourite

Guest suite in Sunderland

5.0 out of 5 average rating, 142 reviews

Bright private suite minutes to Five College area

Welcome to our bright, newly renovated suite in the historic Elihu Smith home, built in 1847. Centered on historic S. Main Street in Sunderland, we are minutes from UMass, Amherst, Hadley, Deerfield, and located on the local bus route connecting directly to UMass and Amherst. Ideal for stays of any length of time, for business or pleasure during any time of the year and walking distance to the Millstone market, as well the Bridgeside Café. Suite is professionally cleaned between each stay.

29 Aug – 5 Sept

$1,279 AUD total

Guest favourite

Guesthouse in Westminster

4.98 out of 5 average rating, 290 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.

15 – 22 Dec

$1,691 AUD total

Guest favourite

Cottage in Orange

4.95 out of 5 average rating, 130 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.

6 – 13 Jan

$1,642 AUD total

Guest favourite

Apartment in Winchester

4.93 out of 5 average rating, 160 reviews

Downtown Loft above Winery and 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!

1 – 8 Nov

$1,084 AUD total

Guest favourite

Tiny home in Orange

4.92 out of 5 average rating, 310 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.

22 – 29 Aug

$1,844 AUD total