Vacation rentals in Bolton

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Top-rated vacation rentals in Bolton

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A quaint cabin is positioned among trees, softly lit at night. An illuminated entrance is framed by colorful pots and surrounded by a cozy seating area with an Adirondack chair. Flickering firelight adds warmth to the inviting outdoor space.

Cabin in Littleton

4.99 out of 5 average rating, 176 reviews

Private & Remote, Enjoy Outdoors, Sleep in Luxury

Bit of a wonderland (57 Acres, 100+ 5-star reviews). A place you won't soon forget. Complimentary firewood, 1/2 hour from Boston, camp but sleep in luxury. This cabin is privately located on a retired Christmas tree farm, about a one-quarter mile off the public road. Listen to the water flow, and watch the sunset over the wetlands. This site is ideally suited for a couple looking for an outdoor experience retiring to the comfort and security of a luxury tiny house. Everything is solar-powered.

Top guest favorite

A charming cabin features a light blue exterior with a sloped roof and welcoming porch. Surrounded by lush greenery, landscaped flower beds with blooming white hydrangeas and evergreen bushes complement the serene setting. A spacious lawn provides ample outdoor space for relaxation.

Guesthouse in New Ipswich

4.95 out of 5 average rating, 358 reviews

"The Porch" Your cozy home away from home!

Welcome to The Porch! Ready for a mini vacation, or just a place to hang out, or work from? You are most welcome here! . This cozy cabin is very flexible and user friendly! It is private to only your group! The downstairs with all it offers, is for one or two person stays. The upstairs becomes available if you enter 3 or more people. This building is in the backyard of our home, as in photos on our Airbnb site, Other info is listed there also! Info book is in room! Welcome! (no pets)

Guest favorite

A winter landscape showcases illuminated ski slopes on Wachusett Mountain, creating a visual contrast against the evening sky. The gentle slopes lead down to the base area, where buildings are warmly lit, presenting a welcoming atmosphere for visitors.

Home in Westminster

4.83 out of 5 average rating, 156 reviews

Lakefront, view of ski mtn, firepit, kayaks, dock

A charming lake house with a magnificent view of a ski mountain — Wachusett Ski Resort (voted #1 in MA). Newly-renovated, 650 square foot cabin with a wall unit AC, fire pit, grill, smart TVs, kayaks, paddle board, and all the amenities you’ll need. (FYI: We also own another lakefront Airbnb right down the street that accommodates 10 guests. Ask for link.) *A brand new retaining wall and dock will be installed May 2024. This will extend and even out the lawn for nights around the firepit!

Top guest favorite

A red tray is positioned on a light-colored dresser, containing a remote control and a white dish labeled 'TRINKETS'. The dish provides a dedicated space for small items, enhancing organization on the dresser.

Guest suite in Hubbardston

4.99 out of 5 average rating, 123 reviews

In-law Apartment, Full Kitchen, Near Mt Wachusetts

Your home away from home is a spacious & newly renovated basement/in-law apartment (approx 1100 sq feet) located below the main house, with its own private entrance, dedicated parking & in walkable neighborhood. The unit has a bathroom, full kitchen, living room & bedroom w/queen bed & extra tv. Hubbardston is a quaint little town with no stop-lights yet conveniently located to many beautiful hiking trails, fishing spots and lakes. 10 minutes from route 2 and 15 minutes from Mt Wachusetts.

Guest favorite

Sturdy wooden steps provide access to the private suite. Lush green landscaping frames the pathway, leading to a level entrance. A handrail is positioned for support alongside the steps, which are designed for easy traversal.

Guest suite in Stow

4.98 out of 5 average rating, 90 reviews

Sisu Suite: Private one bedroom suite

Private suite with separate entrance. Locked door between suite and home. Sitting room with love seat, folding wall-mounted table/desk and chairs, tv, and kitchenette. Kitchenette includes mini fridge, microwave, coffeemaker, water kettle, and toaster. Bedroom with queen sized bed. New bathroom. 25 miles west of Boston. Minutes from pick-your-own apple orchards, winery, cider breweries, and golf courses. Backyard connects to conservation land trails. 3.3 miles from S. Acton Rail station.

Top guest favorite

A serene view from large glass doors reveals a tranquil outdoor area, featuring green grass and trees. A sand garden with small statues occupies the foreground, while a rustic structure and walking path are visible in the background.

Guest suite in Uxbridge

5 out of 5 average rating, 238 reviews

Zen Inspired Retreat with Private Forest Trails

Zig-Zag Trails blends modern comfort with the charm of rural living. Set on 65+ acres of private meadows and forests, our master guest suite is the perfect retreat to relax and recharge. Explore scenic zig-zagging trails, perfect for hiking, mountain and E-biking, and unwinding in nature—a haven for outdoor enthusiasts and homebodies alike. 📍 1 hour from Boston 📍 35 minutes from Providence 📍 25 minutes from Worcester Escape to Zig-Zag Trails—where tranquility meets adventure.

Top guest favorite

A sleek Keurig coffee maker is positioned on a dark countertop, accompanied by a transparent kettle and a glass canister filled with coffee pods. The modern appliances are set against a neutral grey wall, adding a contemporary touch to the space.

Guesthouse in Westminster

4.98 out of 5 average rating, 397 reviews

Guest House - 4 miles from Wachusett Mt.

Welcome to a cozy, newly renovated semi-attached in-law unit! Nestled in a peaceful neighborhood, you’ll be just a short walk from the town center and only a 10-minute drive to the scenic Mount Wachusett. With easy access to Route 2, it’s the ideal base for your adventures. Enjoy the privacy of your own entrance and two dedicated parking spaces. Whether you’re here for a weekend getaway or a longer stay, we’re sure you’ll enjoy your time in this inviting space!

Guest favorite

An exterior view showcases two connected buildings in a serene garden setting. The barn loft is highlighted, featuring a private entrance. Lush greenery surrounds a stone path leading to outdoor seating areas, offering an inviting space for relaxation among the vibrant landscaping.

Guest suite in Littleton

4.91 out of 5 average rating, 403 reviews

Historic Loft with bathroom & kitchenette

A beautiful 1840s barn loft steps away from miles of hiking trails. Fully separate and private entrance, bathroom, and kitchenette. Enjoy a serene, rustic cabin atmosphere with a historic brick hearth and exposed beams. Southeast facing windows overlook patio, garden and ruins. Off the beaten path but only 5 min. to Rte 2, Rte 495, and Boston commuter rail. Drive times w/o traffic: 45 min. Boston, 20 min. Lowell/ Rte 3, Burlington, Bedford, Nashua 30 min.

Top guest favorite

A vibrant sunset casts a gradient of purple and orange hues across the sky, with silhouettes of trees visible in the foreground. The mountain range can be faintly discerned in the distance, providing a serene backdrop to the tranquil scene.

Home in Sterling

4.94 out of 5 average rating, 207 reviews

Quiet country retreat with modern conveniences

Our mountain-view farmhouse sits on a 5 acre knoll, 300' from a quiet country road, surrounded by the sights and sounds of quintessential New England. The location of the property strikes a perfect balance between seclusion and convenience with access to hiking, kayaking, biking, parks, restaurants, grocery, and shopping close by. Restaurant food delivery of local favorites for Japanese (including sushi), Chinese, pizza, sub, salads, etc is available.

Guest favorite

A white door with a grid design stands prominently against a dark green wooden siding. A welcome mat is placed at the threshold, while a lantern and mailbox are mounted to the side. The porch area is partially covered, providing a sheltered entryway.

Apartment in Hudson

4.92 out of 5 average rating, 526 reviews

Newly Renovated Apartment Near Downtown Hudson

Newly renovated private attic apartment near downtown Hudson with kitchenette, living room and bedroom/office. A warm, cozy space with plenty of natural light! Just upgraded to a new king sized bed! Free parking on site Walking distance to restaurants, cleaners, antique shops, roller skating, shopping center, gym, breweries, golf course... & lots more! Nearby there are lots of historical sites, ski areas, and areas for swimming!

Guest favorite

An aerial view captures a serene landscape featuring a calm lake surrounded by vibrant autumn foliage. A building is visible against the backdrop of trees in warm, fall colors, reflecting beautifully on the water's surface.

Guest suite in Marlborough

4.87 out of 5 average rating, 285 reviews

Professional Accommodations!

Across from Lake Williams near 20 and 495, completely separate entrance and parking, all newly renovated, central air, high speed fios internet, 43 inch smart tv, desk, mini fridge, microwave in separate eating area, walk to Dunkin Donuts, Your completely private space! Walk to restaurant with indoor and outdoor seating. For your safety during Covid I keep 72 hours Between guests and have unit professionally cleaned!

Guest favorite

Guest suite in Bolton

4.97 out of 5 average rating, 172 reviews

Vaughn Hill Suite | Dog-Friendly Backyard | Sauna

Tucked into the slope of Vaughn Hill on 3 wooded acres, the entire lower level of our home is yours to enjoy. Cozy 2-bedroom unit with “the BEST BEDS at an Air BNB ever!" to quote one guest. Visit Nashoba Valley Winery (5 min away), get coffee at Harvard General Store (8 min), go apple-picking at a local orchard, or hike Vaughn Hill trails. *Our backyard wood-fired sauna is available by request at $20 per firing*