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Mansion holiday rentals in Orange

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Popular amenities for Orange mansion rentals

Luxury mansion rentals

Top guest favourite
Home in Wardsboro
5 out of 5 average rating, 12 reviews

MtSnow/Stratton Ski Lodge-Hot Tub-Game Room-Pool

ChrisRating, 5 stars1 month ago
This home is Stunning!!! In every aspect! Every room is beautiful and Michelle has thought of every detail to make you feel at home. Incredibly comfortable beds and linens, a fully stocked kitchen for all your cooking/takeout desires, and hang out spot for the kids with air hockey and arcade basketball! I could go on and on. You will not want to leave!
Superhost
Home in Dover
4.81 out of 5 average rating, 36 reviews

MT SNOW Chalet + HOT TUB + new upgrades for 2024!

TraceyRating, 5 stars2 months ago
We had a great weekend at Lisa's house! Lisa was easy to get in touch with and when she knew she might be out of touch she gave us an alternate person to contact. It's snowed overnight during our stay and we were plowed out early to get on the mountain for first tracks. The house is exactly as pictured on the listing, we were very comfortable, and the hot tub was key for relaxing after a day on the mountain. The house has a 80's feel to it, and the wood panelling gives mountain vibes. We had everything we needed for our stay and really enjoyed the time we spent together!
Guest favourite
Home in Southborough
4.88 out of 5 average rating, 164 reviews

Luxury Living at its Best in X-Large 8 Beds Estate

KateRating, 5 stars3 months ago
We had a wonderful 2 day work retreat!! Plenty of space for work colleagues to spread out but many options for us to be together! It was wonderful!
Guest favourite
Home in Otis
4.93 out of 5 average rating, 15 reviews

Spacious Lake Front Home

JeanRating, 5 stars5 months ago
Beautiful location in Otis, right on the lake and so peaceful. The house is very spacious and easily accommodated our family ( 7 adults and 2 children). All the windows in the house provided great views of the lake, especially from the deck. Our host Nick was very responsive when we had questions or any concerns. Would be nice to come for a stay during the summer.
Superhost
Villa in Charlton
4.78 out of 5 average rating, 67 reviews

Winter Home near TreeHouse Brewery with King Beds

CaraRating, 5 stars6 months ago
We got married at a venue about 15 minutes away so we stayed here with our bridal party and the size was perfect. Everyone slept comfortably, we still had plenty of space. The neighborhood is quiet and the location is still close enough for us to enjoy exploring Sturbridge. Michael was responsive and honest with any question I asked!
Top guest favourite
Home in Pittsfield
4.97 out of 5 average rating, 115 reviews

Berkshire Lake- Modern and Updated-close to skiing

LaurenRating, 5 stars1 month ago
Home was beautiful, clean and close to Jiminy Peak, 16 minute drive! Great kitchen and living area to hang out
Guest favourite
Cabin in Great Barrington
4.96 out of 5 average rating, 76 reviews

Modern Luxury Log Cabin

TerryRating, 5 stars2 months ago
Tim was a great host of a great house. We had a family of 8 including 3 kids and were so comfortable and felt that the house was clean, well-stocked, and welcoming. Tim responded to any questions within minutes and was so accommodating. Would recommend to anyone and everyone.
Guest favourite
Home in Berlin
4.88 out of 5 average rating, 16 reviews

Luxurious Spacious Haven Retreat - Close2Boston

AprilRating, 5 stars3 weeks ago
I’ve never stayed at such a stately home! Gorgeous home on top of a hill with only one other house around. Nice pond to see from the lovely front porch. Or you can relax on the back deck, where it is nice and peaceful. The kitchen was amazing and huge. The only thing we could have used were wash cloths. Host was very kind and responsive with us.

Pet-friendly mansion rentals

Guest favourite
Cabin in Jamaica
4.88 out of 5 average rating, 112 reviews

Cozy Log Cabin near Stratton/Mt. Snow-pet friendly

JamesRating, 5 stars2 months ago
Christina was an excellent host who ALWAYS responded to any of my questions or concerns immediately and courteously. Her space was exactly as described and very spacious as well as a fantastic environment for a group to get together and have a great time! I highly recommend Christina’s place for a great time with a large group, she is the ideal host who works tirelessly to provide an amazing space for her guests!
Guest favourite
Home in Salem
4.98 out of 5 average rating, 191 reviews

Magical Farm Getaway - a must visit!

StephanieRating, 5 stars2 months ago
A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!
Top guest favourite
Home in Brattleboro
4.94 out of 5 average rating, 121 reviews

Spacious Brattleboro home on river, walk to town

DebbieRating, 5 stars2 months ago
Absolutely incredible place! Tons of room, bathrooms for each bedroom was a big hit. Amazing location. Views were magnificent after 8 inches of snow and some freezing rain. Perfect excuse to not leave the house and enjoy the peaceful serenity over a nice margarita. Fall views must be totally awesome. Don’t need to bring anything except you, your friends and some food. The home has everything you need, all set and ready to go, and I mean everything you’ll need. The house manager Teri was an absolute peach. Her connection to the house and knowledge of the local history was amazing. 5 STARS doesn’t do this place justice. Already planning a return visit.
Superhost
Farm stay in West Brattleboro
4.94 out of 5 average rating, 132 reviews

Lilac Ridge Farm House

MatthewRating, 5 stars4 months ago
We had a great stay at Lilac Ridge! The house was near and spacious, plenty of room for our family. We stayed in quite a bit and enjoyed the farm (including a visit with the calves!) and the house. The little farm stand had some nice things, including fresh eggs, maple syrup, honey, and soap, all local. Ross and Amanda were super responsive and took care of all our needs. Thanks so much!
Top guest favourite
Chalet in Dover
4.98 out of 5 average rating, 109 reviews

Mountain Chalet: Private Brook - Hot Tub - Firepit

EricRating, 5 stars1 month ago
Family had a great stay at Danielle and Ben’s the house was very clean and kid friendly and we really enjoyed having the view of the creek from decking area. Very close to Mt Snow and surrounding area restaurants and attractions. Would stay again.
Guest favourite
Chalet in Jamaica
4.82 out of 5 average rating, 171 reviews

Artists Chalet minutes from Stratton Ski Resort

DevonRating, 5 stars1 month ago
We had a great weekend at Joe’s place! For my son’s 12th birthday we wanted to ski all day and a cozy place to come home to- this house provided all of that! Joe was extremely responsive with a few questions we had, the place was spotless and accommodated our party of 9! A quick ride to Stratton- we’ll be back next winter!
Top guest favourite
Home in New Salem
4.89 out of 5 average rating, 215 reviews

Stone n' Sky Lodge

JasonRating, 5 stars5 months ago
I genuinely don't know what to say other than the fact that this may be one of the greatest places I've had the honor to lodge at. I did a lot of vetting across New England to find a wonderful place that could sleep a decent amount of people, provide a scenic and comfortable escape, and keep us entertained. Sarah's wonderful Stone and Sky Lodge exceeded every expectation I just listed. It's cozy, warm, and feels like a hidden nook! The scenery and nature couldn't be more beautiful. I never got the pleasure to meet Sarah, though I wish I did. Over messages and from what my friends told me, I just know that Sarah is the most hospitable and kind host that I've talked with in a while, and I hope that next time I can thank her personally. From my friends and I, we thank you for sharing your home with us. If you think that the excellent reviews are too good to be true, don't. This IS the truth, and I can't wait to have another reason to come back to this wonderful treasure of a place.
Guest favourite
Home in Great Barrington
4.96 out of 5 average rating, 166 reviews

Elegant Year-Round Lakeside Retreat with AC

CristinaRating, 5 stars1 month ago
For our fourth stay at Katie and Greg's, we were just as satisfied as the first x3 trips! And we're already planning our 5th! Truly a gem of a home and wonderful hosts. Highly recommend!

Mansion rentals with a pool

Top guest favourite
Home in Cambridge
4.97 out of 5 average rating, 39 reviews

Country hideaway

GwenRating, 5 stars8 months ago
Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!
Guest favourite
Home in Hopkinton
4.95 out of 5 average rating, 153 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

RenaeRating, 5 stars1 week ago
Six of us stayed over the weekend. We were very comfortable and Brad was very helpful and responsive. House had everything that we needed. Brad is a great host. Would 100% recommend a stay.
Superhost
Home in Winchendon
4.95 out of 5 average rating, 22 reviews

Amazing Lakefront Home with Pool- Tatum's Place

NidhiRating, 5 stars1 week ago
Great stay overall — just be mindful of seasonal comfort! We had a lovely time at this beautiful property — it’s well-maintained, peaceful, and has a lot of charm. The host was responsive and check-in was easy. Just a heads-up for future guests: the property has seasonal settings, so you’ll either get heat or A/C depending on the time of year, not both. It made things a bit uncomfortable during a weather transition, but manageable. Still, the beauty and uniqueness of the space definitely made up for it. Would recommend with that one caveat in mind!
Guest favourite
Home in Woodstock
4.94 out of 5 average rating, 235 reviews

Cedar Ridge: House or House+Apartment

SuzanneRating, 5 stars1 month ago
We love the house! It’s spotless (very clean), very comfortable and super peaceful in a beautiful location! Highly recommend!
Guest favourite
Home in New Lebanon
4.98 out of 5 average rating, 59 reviews

Berkshire Mountain home views, pool, Queechy Lake

GeorgeRating, 5 stars2 months ago
The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!
Superhost
Home in Lee
4.87 out of 5 average rating, 30 reviews

* Private Berkshire Escape* Monthly Pricing Avail

JoanRating, 5 stars9 months ago
This gem of a house served as home base for my family of 4 when visiting Tanglewood & Berkshires area for a long weekend! The house is artfully decorated, with unique treasures we enjoyed exploring, common spaces for us to hang together as a family plus plenty of room for us to spread out for privacy. We especially enjoyed having the pool onsite, backyard fire pit, and multiple outdoor seating areas. Teva was a very responsive, helpful host! Went above and beyond! Thanks for an excellent stay!
Top guest favourite
Home in Great Barrington
4.99 out of 5 average rating, 69 reviews

Stunning luxury home with pool

LaurieRating, 5 stars2 weeks ago
What a spacious, luxurious retreat! My family and I completely enjoyed our stay in Prem and Mary’s beautiful home. Plenty of room to spread out and relax, high-end appliances, top-notch bathrooms and comfortable bedding all made for a happy and pampered stay. We loved sitting up late together around the gas fireplace on the enclosed porch and wow what a treat to have a grand piano in the house (haven’t played one in 30 years!). The house is perfectly located between the charming towns of Stockbridge and Great Barrington, with all the area attractions and restaurants, breweries, etc only a short drive away. Prem and Teagan, the house manager, were so friendly and helpful and responded immediately to any questions we had. Delightful stay in every way and we look forward to a return visit!
Guest favourite
Home in Wilmington
4.84 out of 5 average rating, 171 reviews

The Vermont Barn (Mount Snow)

AmandaRating, 5 stars2 months ago
My family loved staying here! There was plenty of snow for activities. We went skiing at Mount Snow and ice fishing on Lake Raponda for a day. The barn is so unique and had everything we needed. There were lots of extra pillows and blankets and a big cozy couch to curl up and relax by the wood stove. Having access to the clubhouse was amazing… the kids loved swimming in the warm pool after a long day outside. Brian was super responsive and easy to talk to! We already want to go back!

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