Vacation rentals in Ashby

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Top-rated vacation rentals in Ashby

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

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Guest favorite
A lakefront cottage is positioned among trees, with a spacious lawn leading down to the water. A newly installed dock extends into the lake, while various colorful kayaks and paddle boards are neatly arranged on the grass. The sun sets, casting a warm glow over the scene.
Home in Westminster
4.89 out of 5 average rating, 239 reviews

Lakefront, view of ski mtn, fireplace, sauna

Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

Top guest favorite
A quaint cabin sits amidst lush greenery, framed by tall trees. The blue exterior features a welcoming porch, flanked by blooming white hydrangeas. A well-kept lawn complements the serene landscape, providing a peaceful retreat in a natural setting.
Guesthouse in New Ipswich
4.95 out of 5 average rating, 431 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)

Top guest favorite
The exterior of The Ginger Bed is showcased, featuring a light green facade with white trim around the windows and door. A welcoming orange door is prominently displayed, surrounded by a landscaped area with colorful mums and autumn foliage.
Guest suite in Ashburnham
4.98 out of 5 average rating, 542 reviews

The Ginger Bed King Suite

Come for the lovely country setting, the winter beauty, amenities, neighborhood, convenience, privacy, spaciousness, and the comfortable bed. Close to many wonderful hiking/biking paths, rail trails, Wachusett ski area, Jewel Hill, Lake Wampanoag, Kirby area. WI-FI, TV ( Hulu and Netflix), refrigerator, microwave, coffee/tea maker, reading lights, table area, continental breakfast, parking... Good for couples, solo and business travelers. (Key pad for Covid safe entry) Everyone is welcome!

Top guest favorite
A cascading waterfall flows over natural rocks, surrounded by lush greenery. Delicate pink flowers in the foreground enhance the serene setting, where the sound of rushing water and natural beauty create a peaceful atmosphere.
Guesthouse in Wilton
4.94 out of 5 average rating, 691 reviews

Cottage beside a waterfall

Our 1840’s renovated grist mill is located in the beautiful Monadnock Region. The house and cottage are situated on twelve acres and includes gardens, an orchard, berry bushes, grape vines, beehives, a dog, and a tremendous waterfall. We are close to many of nature’s gems including Mount Monadnock, Pack Monadnock, the Heald Tract hiking trails, skiing, snowshoeing and swimming. Also the acclaimed MacDowell Arts Center, Andy’s Summer Playhouse, Andres Institute of Art and the Waldorf Schools.

Guest favorite
A modern ranch-style home is set against a backdrop of lush greenery, featuring a combination of wood and large glass windows. Solar panels are visible on the roof, with a stone wall and landscaped area framing the exterior. The property blends harmoniously with the surrounding nature.
Home in Amherst
4.97 out of 5 average rating, 101 reviews

Modern Luxury in a Spectacular Natural Setting

The Pond House is a hidden gem: A Frank Lloyd Wright-inspired modern ranch on 6 acres, with a private pond. Equal parts modern architecture and natural beauty, our secluded property is the perfect place to unwind in solitude, or use it as a base for local adventures. Under vaulted ceilings, endless windows and the screened porch offer seamless indoor-outdoor living in a stylish space. Explore the woods on our 1/4 mile of private paths, or enjoy a campfire at the edge of our private pond.

Top guest favorite
Home in Ashburnham
5.0 out of 5 average rating, 39 reviews

The Nutty Bird Lakehouse

Charming lakefront featuring 2 cozy bedrooms comfortably accommodating up to 4 guests, w/2 bathrooms. Nestled in nature, this home offers breathtaking lake views—perfect for relaxing with a good book and a hot cup of coffee. Enjoy the propane firepit on lower deck. For those looking for adventure, each season brings unique activities: swim, hike, and fish in the summer, or enjoy ice skating, sledding, snowshoeing, & scenic drives in winter. Embrace the beauty and tranquility year-round!

Top guest favorite
A grassy backyard extends towards a calm lake, with a wooden deck featuring a barbecue grill. In the background, a row of chairs lines the shore, complementing the natural setting of trees and water.
Home in Ashburnham
4.96 out of 5 average rating, 70 reviews

Lake House with island and boats to cruise on!

This is a wonderful place to put aside your busy life. No matter the season, our lake home is the feel of relaxation, cozy and comfort. Whatever yours is, you will have the best of all seasons here. Spring flowers popping up, summer water fun, beautiful fall foliage and winter ice-skating, just to name a few. Start the day with a warm cup of coffee watching the sun rise over the trees. Fill the rest with fun and adventures. Finish it with a campfire, s'mores and a nice glass of wine.

Top guest favorite
A modern home features a combination of dark siding and natural wood accents, positioned among tall trees. A welcoming porch extends from the entrance, complemented by an American flag. The surrounding area includes a gravel path and vibrant greenery, providing a serene atmosphere.
Home in Jaffrey
4.98 out of 5 average rating, 107 reviews

Willow Falls Home ~Hot tub & Waterfront

Constructed waterfall views are just feet away from you! Not far from Boston, RI or CT, this newly designed home is located at a privately viewed pond, in New England, near Mt. Monadnock! Kick back, relax & listen to the water falling in a screened-in gazebo, or in the outdoor hot tub! Or view it all at the picture windows and enjoy the solitude at this picturesque retreat! Inside you'll find multiple lounging areas, luxurious beds, a fully stocked kitchen and a fun game room.

Top guest favorite
A bright yellow two-family home is positioned amidst greenery, featuring a welcoming entry with a red door. A small flowering tree adds a splash of color in front, while a large deck is visible in the background, perfect for outdoor gatherings.
Home in Chelmsford
5.0 out of 5 average rating, 260 reviews

Newly renovated, spacious, clean, 3 bedroom home.

Whether traveling for business or pleasure, this ideally located, pet-friendly home in North Chelmsford, Massachusetts, is accessible to major highways and commuter rails. The home is close to major hospitals, universities, and concert venues. The area is rich in America’s history and is surrounded by historical sites to visit all within minutes. The beautiful, light, airy living space boasts all the comforts of home. Our goal is to give you the best travel experience possible.

Top guest favorite
A warm kitchen area features wooden paneling and a round dining table set for two. A small, cozy electric stove is situated near the table. The space is complemented by a full-size refrigerator and a microwave, with decorative touches on the walls.
Apartment in New Ipswich
4.96 out of 5 average rating, 143 reviews

Quiet country apartment in farmland setting.

Cozy studio located on 90 acres of private property that includes conservation woodland and fields, perfect for a challenging hike and wildlife viewing. Apartment has 1 queen bed with roll out cot and a full bathroom with shower and selection of towels. The fully equipped kitchen comes with a refrigerator, microwave, and the washer and dryer downstairs mean less packing. When not out and about exploring the countryside there is WiFi and a smart TV to keep you entertained.

Guest favorite
A serene bedroom features dark walls and a vintage wooden headboard above a spacious bed adorned with decorative pillows. Light enters through the window, illuminating the room's elegant rug and providing a cozy atmosphere. Nightstands with lamps flank the bed, enhancing the inviting feel.
Home in Fitchburg
4.95 out of 5 average rating, 131 reviews

Guest home in downtown Fitchburg

10% off if booking 1 bedroom only. Exclusive use of the house but please do select the correct number of guests to display the final fee. Spread out in this centrally-located (downtown/urban) home built in the 1800s - where each room has been curated in a timeless tone, with relaxation and comfort in mind. Convenient to FSU, Game On Sports Complex, Fitchburg Art Museum, the commuter rail to Boston, Applewild School, Wachusett Mountain, Great Wolf Lodge etc.

Guest favorite
A comfortable sofa is positioned near a window with sheer curtains, allowing natural light to illuminate the space. A decorative pillow with text is placed on the sofa, while a glass of wine rests on a wooden table outside, visible through the window.
Cabin in Winchendon
4.96 out of 5 average rating, 136 reviews

The little house on Mirror Pond

Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

Popular amenities for Ashby vacation rentals