House vacation rentals in Rockingham

Reillys Rest -GreenMtns! Secluded-Pet-Kid friendly

Reilly's Rest is a private home located on its own 6 acres in a prime location to SKI, HIKE, FISH, SWIM, KAYAK, WALK, + RELAX in the Green Mtns! 11/19 New floors-windows-appliances! The home is just 7 miles to Magic, 10-Bromley, 15-Stratton , and under 20 to both Okemo & Manchester. Reilly's Rest provides a peaceful + cozy stay on 6 acres with Mtn. views. Our Vermont contemporary-style home is sure to impress with warm wood interiors and an upstairs with open floor plan and beautiful views!

Value · Family · Sleep quality

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to

Value · Family · Outdoor spaces

Luxury Mid-Century Modern Vermont Home, Okemo View

The Brewster House is a premiere destination for skiing, hiking, enjoying the country or just lounging by the pool. Designed by renowned mid-century modern architect turned painter George W.W. Brewster, the Brewster House has been lovingly restored and updated, and filled with original, local art. With gorgeous views of Okemo and Hawks Mountain Wildlife Area, the Brewster House is close to incredible dining, great art galleries, and antique shops. Come bask in beauty and relax completely!

Location · Family · Walkability

Ski Mountain View Estate

Pool is open for the summer of '26 Have fun in Vermont with the whole family at this peaceful off the grid feeling private home. Come see the amazing, scenic views Vermont has to offer. We are located minutes to some great ski mountains if you are looking to ski or snowboard. Love hiking? Enjoy hiking right out back of our home. Great time for the kids and parents to have a sledding party with a fire and views. Then relax in the new hot tub right off the deck. Great multi family getaway

Location · Family · View

Private & Cozy Farmhouse in New Hampshire

Escape to our relaxing farmhouse in a quiet corner of Charlestown, NH. Overlooking farm fields, old barns and the Connecticut River, this property is the perfect quiet getaway! The house is within walking distance of the river as well as downtown Charlestown. It is located between Claremont, NH and Keene, NH making it a great midway point to access both for shopping, area attractions and a number of ski resorts. Minutes from I-91. Come and make yourself at home in this private getaway!

Family · Value · View

The Deanery - Grafton Vermont

Welcome to The Deanery in Historic Grafton! Located in a great spot, less than 1/10 of a mile (a two-to-three-minute walk) from the Grafton Inn! Grafton is a quaint, quintessential town that makes for a great place to relax with family and friends. There is a local market, pub, and the Grafton Ponds - all within walking distance. Check out our feedback to hear from others who have enjoyed The Deanery! We also offer discounts for weekly stays and returning guests. Please ask.

Location · Family · Quiet

Vermont 1828 Reunion House, near Okemo

The Vermont 1828 Reunion House, close to Okemo is a spacious historic vintage ski lodge and farmhouse with 2 kitchens, 8 bedrooms, 4 baths, & a quintessential Vermont character. Excellent for gatherings & family reunions. Linens & towels provided, beds made. 10 acres, meadow & hidden pond. . A new automatic sprinkler system was installed in 2024 & the house complies with all safety regulations & certified by the town of Chester. Must be 25 years to rent. Long term rentals possible.

Family · Value · Layout

Charming Chester Farmhouse Near VT Slopes

Unplug at our spacious 4-bed Chester farmhouse, a four-season retreat minutes from Okemo, Magic & Bromley. Highlights: *Chef’s kitchen & coffee bar *Fast Wi-Fi, dedicated workspace & Smart TV *Spacious backyard for dining & stargazing *Easy 10–20 min to skiing, hiking & local towns *Pet-friendly, family-ready Spend your days hiking, swimming, leaf peeping, or exploring nearby towns. In winter, hit the slopes, then gather for games and a movie. Book your Vermont getaway today!

Location · Family · Laundry

Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain

Ideal to host up to 6 guests, this home on 2 acres of land is a perfect retreat for anyone looking to be in the heart of nature. Chester and Ludlow, VT are minutes away and call you to explore historic landmarks and enjoy skiing at Okemo Mountain (located 15 minutes away). With modern facilities & a private location, this will be your home away from home! New in June 2024 - we added a large outdoor patio equipped with a Jacuzzi Hot Tub, Fire Pit, and picnic table.

Family · Location · Getting around

Modern 3-bedroom A-frame in Londonderry w/ Pond

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min). STR License 26-23-185

Family · Location · Sleep quality

Artistic Southern Vt Countryside Home at Windham

Escape to 3.5 private acres in the Green Mountains. Art-filled spaces, Tempur-Pedic beds, A/C, two living rooms, full kitchen with gas stove. Groomed trails and berry foraging outside your door. Fire pit with valley views. Minutes from waterfalls, swimming holes, the Appalachian Trail, and Londonderry dining. Magic Mountain under 10 min, 4 more ski areas nearby. Pellet stove, generator, dedicated workspace — perfect for remote work or a mountain reset.

Family · Value · Indoor spaces

Peaceful Beautiful Mountain Home Spectacular Views

15 Spectacular Acres! Plenty of room for the entire family or great for a couples getaway. This home has everything you need. There are brand new mattresses, quilts, linens, towels, cookware, plates and utensils for your comfort. The beautiful mountain views are seen from just about every room. There is a wood burning fireplace, 4 bedrooms and 2 full bathrooms. Both levels have 3 season porches to enjoy the views, coffee, reading or a meal.

Location · Family · Backyard