Summer stays

Properties at their best in summer

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Sleeps

10 properties found

Villa at Bear Creek
Villa at Bear Creek

Bartlett, NH

A 9,000 sq ft castle-inspired Italian villa on 6 secluded acres in the White Mountain Valley. Perfect for large group getaways, family reunions, and wedding events — with private trails, streams, ponds, and easy access to Attitash and Wildcat ski resorts.

White Mountains Sleeps 16
Chateau Worthington Estate
Chateau Worthington Estate

Worthington, MA

A grand luxury chateau on 12 acres at the edge of the Berkshires with an indoor pool, gym, and expansive entertainment spaces. Ideal for large group getaways near Tanglewood, Shakespeare & Company, and the area's ski resorts.

Western MA Sleeps 24
Chateau Worthington — Main House
Chateau Worthington — Main House

Worthington, MA

A grand luxury chateau on 12 acres at the edge of the Berkshires with an indoor pool, gym, and expansive entertainment spaces. Ideal for large group getaways near Tanglewood, Shakespeare & Company, and the area's ski resorts.

Western MA Sleeps 16
Chateau Worthington — Carriage House
Chateau Worthington — Carriage House
4.97

Worthington, MA

Once a private recording studio and artist's loft — home to Kevin Eastman (TMNT co-creator) and Aaron Lewis (Staind) — this rustic Berkshires carriage house blends creative history with New England charm. Pool table, 3 bedrooms, and countryside views.

Western MA Sleeps 8 Dog-friendly
The Black Boar Inn
The Black Boar Inn
4.85

Ogunquit, ME

Built in 1674, The Black Boar Inn is one of the oldest wooden structures in the United States. This historic 7-bedroom inn in the heart of Ogunquit is a 3-minute walk to the beach, with a separate Beach Rose Cottage and walkable access to restaurants, galleries, and the Marginal Way.

Coastal Maine Sleeps 13
The Moonstruck
The Moonstruck
4.89

York, ME

A classic 5-bedroom Maine cottage with ocean views, AC, and a private backyard — dog-friendly and a short walk to Short Sands Beach and downtown York. Perfect for families and groups who want the beach without giving up the comforts of home.

Coastal Maine Sleeps 13 Dog-friendly
Mountain-View at Sunday River
Mountain-View at Sunday River
5

Newry, ME

A stunning 5-bedroom mountain lodge with panoramic views, a private hot tub, and a grand stone wood-burning fireplace — just 4 miles from Sunday River Resort. Ideal for families, friend groups, or wedding parties seeking mountain serenity close to every adventure.

Western Maine Sleeps 12 Dog-friendly
The Birchside
The Birchside
4.96

North Conway, NH

A beautifully restored 1873 inn in the heart of North Conway Village — 7 bedrooms, 6 baths, and a private hot tub. Walk to shops, restaurants, and the Conway Scenic Railroad, with Attitash and Cranmore ski resorts minutes away. Dog-friendly with a fully-fenced yard and multiple decks.

White Mountains Sleeps 16 Dog-friendly
The Conway Farm Coming Soon
The Conway Farm

Conway, MA

An 82-acre farm in the hills of Conway, MA — coming soon as a premier wedding and private event venue. Ceremonies and receptions will be hosted under a tent behind the barn, with the full farm property as your backdrop.

Western MA 82 acres · Wedding venue
Wentworth Condo — Fireplace, A/C
Wentworth Condo — Fireplace, A/C
4.82

Jackson, NH

Stay at this charming, dog-friendly condo at The Wentworth, a historic resort in the heart of Jackson Village. Step outside to cross-country ski trails or the golf course, and enjoy quick drives to Black Mountain (5 min), Attitash/Bear Peak (10 min), Wildcat or Cranmore (15 min).

White Mountains Sleeps 6 Dog-friendly
Wentworth Townhome — Walk to Dining, Ski & Golf
Wentworth Townhome — Walk to Dining, Ski & Golf
4.95

Jackson, NH

Escape to this three-level condo at The Wentworth in Jackson Village — your gateway to the White Mountains. Across from groomed cross-country trails and minutes from downhill gems like Attitash, Wildcat, Black Mountain, and Cranmore.

White Mountains Sleeps 6