Holiday rentals in Ashby

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Top-rated holiday rentals in Ashby

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

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Guest favourite

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

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

LocationFamilyIndoor spaces

4.89 out of 5 average rating, 242 reviews

Guest favourite

A serene view of a tranquil quarry, showcasing calm waters reflecting the surrounding greenery. Kayaks and floats are arranged near the water's edge, inviting relaxation and exploration. The natural rock ledge adds texture to the landscape, enhancing the peaceful atmosphere.

Villa in Milford

Water's Edge~Peak Foliage~Kayaks~Fire Pit~Hot Tub

Perched at the water's edge facing stunning 80ft granite cliffs ablaze with fall foliage! Cliff House on historic quarry offers breathtaking beauty year-round. Cozy up by the new gas fireplace in the sunken living room with heated floors, or warm up at the outdoor gas fire pit. Master suite with private balcony & spa bath, secret bookcase kids' room, game room, movie theater, hot tub. Dock with kayaks & paddle boards. Snowshoes provided, ski slopes 30 min away! A sanctuary for lasting memories.

FamilyValueWalkability

4.96 out of 5 average rating, 107 reviews

Top guest favourite

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

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!

FamilyLocationLong stay

4.98 out of 5 average rating, 546 reviews

Top guest favourite

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.

Guest house in New Ipswich

"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)

LocationFamilyHiking

4.95 out of 5 average rating, 435 reviews

Top guest favourite

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.

Guest house in Wilton

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.

ValueFamilyBreakfast

4.94 out of 5 average rating, 695 reviews

Top guest favourite

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

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.

FamilyLocationBathroom

4.96 out of 5 average rating, 70 reviews

Top guest favourite

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

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.

ValueFamilyCheckout

4.98 out of 5 average rating, 111 reviews

Top guest favourite

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.

Flat in New Ipswich

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.

LocationFamilyAccess

4.96 out of 5 average rating, 144 reviews

Guest favourite

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

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.

ValueLocationDecor

4.93 out of 5 average rating, 133 reviews

Top guest favourite

Home in Mason

Whittier farm house at Barrett Hill Farm

Experience the best of New Hampshire country living in this charming cape- style home. Nestled on the edge of rolling fields. Our home offers private driveway and a secluded yard- perfect for morning coffee with a view of the farm fields. A short walk brings you to our farm store open daily 8am-6pm. Stock up on our fresh farm raised meats, in season vegetables and fresh picked fruit to cook in your private kitchen. We host several events on the farm.

LocationFamilyNearby

4.96 out of 5 average rating, 26 reviews

Top guest favourite

Home in Ashburnham

The Nutty Bird Lakehouse

Escape to the Nutty Bird, a charming lakefront cottage with 2 cozy bedrooms, 2 baths and room for 4. Wake to beautiful lake views, sip coffee by the water, kayak, swim, fish or hike, then unwind by the propane firepit. Cooler months bring colorful foliage, scenic drives, snowshoeing, sledding and skating. Cozy, peaceful and stocked with the comforts of home, it’s the perfect place to slow down, reconnect and enjoy New England lake life year-round.

FamilyLocationKitchen

5.0 out of 5 average rating, 44 reviews

Guest favourite

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

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.

FamilyLocationKitchen

4.96 out of 5 average rating, 139 reviews