Mansion holiday rentals in Orange

Stone n' Sky Lodge

Complete with all the comforts & amenities of home, Stone n’ Sky Lodge is fully furnished & decorated with family heirlooms & fine art. Featuring a fully equipped kitchen, fiber optic internet & a separate home office, the Lodge is located on a paved, dead end road, surrounded by a wildlife sanctuary; yet minutes from town & interstate highways. Local attractions, festivals, artisans, hiking, micro-brewed beers, ciders, good food & music are all to be discovered within minutes of this location.

The Lodge on Warner Hill

On your journey to our lodge, you will pass through a nostalgic covered bridge, drive by a babbling brook, and meander up a winding dead-end dirt road. Our home sits in a quiet, peaceful 5-acre setting. It has been completely remodeled with earth-tone charm. Enjoy your time with friends and family relaxing, reading a book, playing pool, barbequing on the back deck, gazing at the stars, or hanging out by the fire pit. Located less than 10 minutes from Berkshire East and the Deerfield River

Perfectly Polished Deerfield Home 5 min to I-91

A perfectly polished home, nestled in the Sugarloaf Mountain Range with a view of Mount Toby! This property offers 4 bedrooms and 4 beds. With over 2000 sqft of living space, you will enjoy coming home to wind down after a day at Yankee Candle, hiking, or other event in the beautiful Pioneer Valley. The house has something for everyone, whether it’s streaming your favorite show on Netflix, Hulu or Prime Video or relaxing on the patio deck while the kids enjoy the huge pool and water slide!

Lovely & Peaceful Waterfront Vacation Retreat

Come enjoy this unique & beautiful retreat home, set on 50 acres of wooded land, with a breath-taking view over a 2 mile long, 190-acre body of water, & no houses in sight! Wonderful in any season. Peaceful, healing haven, & great get-away spot for a romantic weekend or family vacation. Perfect for swimming, boating, fishing, hiking, & cross-country skiing--or just relaxing in a hammock, on the deck, or in a bedroom overlooking the water. Youtube Video: Fred's Place, James Crowther

Colrain Winter Adventure HotTub AirHockey Firepit

Escape to Millhouse 254, a historic 5-bedroom home blending modern luxury with classic charm. Perfect for large groups & families, it comfortably sleeps 10 and features a hot tub, game room, and an accessible main-floor suite. Located just 5 minutes from the shops and restaurants of Shelburne Falls, it's your ideal retreat for exploring the outdoors or simply relaxing in style. Enjoy a fully equipped kitchen, private yard, and year-round fun in this thoughtfully updated home.

4BR Cabin w/ Hot Tub & Pools –15 mins to Mt Snow

Family-friendly cabin in Chimney Hill, just 15 min to Mount Snow & 35 to Stratton! Relax in our 4BR, 2BA home with a hot tub, indoor and outdoor pools, fire pit, clubhouse gym, fully equipped kitchen & cozy living spaces. Sleeps 8 comfortably (King, Queen, Full + trundle, 2 Twins) with a Pack ’n Play for little ones. Perfect for skiing, hiking, or unwinding year-round. Enjoy mountain charm, modern comfort, and easy access to trails, lakes, and Wilmington’s shops & dining.

The Suprenant House

Cozy home in the 5 college area, close to downtown Amherst minutes from UMASS and Amherst College in a rural part of Town with endless scenic views. Free fast Wifi and parking. During your stay you can enjoy a fully stocked kitchen, laundry essentials, books, board games and other activities. Your hosts live directly next door to the property and available to help at any time. You will be staying next to a working farm, where there are trucks and machines working daily.

Peaceful cabin close to skiing & Brattleboro

Country privacy close to the best of Southern VT! This spacious home is close to skiing (20 min to Mt. Snow; 35 min to Stratton), river swimming holes, hiking, biking, art galleries and great restaurants. Open concept with fireplace, cook's kitchen, jet bathtub, gardens, winter hot tub off deck, and large patio and fire pit give the perfect vibes for your VT gathering. Secluded from neighbors but close to amenities, this home is a comfortable and peaceful retreat.

MountSnow 8 Min, HotTub, GameRoom, FirePit, DogsOk

✔ Relax in the Hot Tub under the Pergola & String Lights ✔ Cozy Fire Pit Area with Adirondack Chairs ✔ Fun Game Room with Air Hockey & Connect Four ✔ 4 Bedrooms, 3 Bathrooms ✔ Dog-Friendly (w/ fee) ✔ 8 Minutes to Mount Snow, 30 minutes to Stratton, 60 minutes to Okemo ✔ 20 minutes to Lake Whitingham/Harriman Reservoir for boating & fishing ✔ Fast Wi-Fi for Remote Work & Streaming ✔ High Chair & Pack N' Play Provided ✔ All Linens, Towels, & Soaps Included

Modern 4BR Retreat | Walk to Mount Holyoke + Town

Welcome to our bright, fully renovated 4-bedroom retreat in the heart of South Hadley! This spacious first-floor apartment blends vintage charm with modern style—featuring a sleek kitchen, cozy living room, and fully renovated bathroom. Walk to Mount Holyoke College and Village Commons, or take a short drive to nearby Smith, Amherst, Hampshire, and UMASS (all within 20 minutes). This central location is great for families, visitors, or a peaceful getaway!

Spacious Brattleboro home on river, walk to town

Spacious 3,000 sq. ft. home with 4 bedrooms (3 queens, 2 twins) and 4 bathrooms, 3 en-suite. Enjoy a formal living room with grand and upright pianos, a cozy TV room, and a fully equipped kitchen with eat-in area leading to a deck with stunning river and mountain views. Formal dining seats 12. Expansive grounds are perfect for relaxing or hosting special events. Just a 10-min walk to Brattleboro’s Main Street shops, cafes, and culture.

The 1770 House

It’s ski time at Berkshire East. Come and enjoy our country retreat with breathtaking mountain and valley views. This expanded 1770 farmhouse gives you 4,500 sq. ft. of space for large family and friend get togethers. The house overlooks the Green River Valley with views to Vermont. The end of a dirt road location provides an escape with views that are changing through the seasons. There are six bedrooms and three bathrooms.