Vacation rentals
for every season

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.

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.

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.

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.

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.

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.

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.

A serene penthouse retreat perched atop a historic brick townhouse on one of Boston's most photographed gas-lit streets. Two king bedrooms, two baths, and a 99/100 walk score — steps from the Public Garden, Boston Common, and Charles Street.

A luxe 2-bedroom brownstone unit in Beacon Hill's most prestigious historic district, just off Louisburg Square and parallel to Charles Street. 99/100 walk score, easy T access, and a patio — new to EverSeason.

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.

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.

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).

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.