Vacation rentals in Phillipston

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Top-rated vacation rentals in Phillipston

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Top guest favorite

Cottage in Petersham

4.99 out of 5 average rating, 218 reviews

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Top guest favorite

Home in New Salem

4.9 out of 5 average rating, 227 reviews

Stone n' Sky Lodge

Complete with all the comforts & amenities of home, Stone n’ Sky Lodge is fully furnished & decorated with family heirlooms & fine art. Featuring a fully equipped kitchen, fiber optic internet & a separate home office, the Lodge is located on a paved, dead end road, surrounded by a wildlife sanctuary; yet minutes from town & interstate highways. Local attractions, festivals, artisans, hiking, micro-brewed beers, ciders, good food & music are all to be discovered within minutes of this location.

Top guest favorite

Guest suite in Ashburnham

4.98 out of 5 average rating, 488 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!

Guest favorite

Guesthouse in New Ipswich

4.95 out of 5 average rating, 387 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

Cabin in Winchendon

4.96 out of 5 average rating, 73 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 (our apologize but it is currently not working) 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.

Top guest favorite

Guest suite in Hubbardston

4.97 out of 5 average rating, 153 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

Loft in Peterborough

5 out of 5 average rating, 207 reviews

Peaceful Mill on the Water - Home Away from Home

Immerse in tranquility at our serene mill retreat in Southern NH. This historic space, adorned with original timber, rustic brickwork, and lofty 11 ft ceilings, offers a spacious 2,650 sq ft sanctuary. Relax in the soaking tub, or savor the calming waterfall views from the deck. Conveniently near downtown, but distant enough for undisturbed peace. Welcome to your soothing retreat for rest and rejuvenation. A remote worker's dream office with high speed connectivity and dedicated workspace.

Top guest favorite

Apartment in Athol

5 out of 5 average rating, 13 reviews

Dwelling Place

Welcome to Dwelling Place Unwind at our peaceful, open-plan carriage house apartment, tucked away on thirteen wooded acres. Seeking adventure or relaxation, this is your perfect escape. Minutes from recreation-rich lakes and trails of the north Quabbin; easy access to hiking, kayaking, leaf peeping, and snowshoeing. Also close to golf, disc golf, and an equestrian center. Return to tranquility to rest, recharge, and experience a true retreat in nature—perfect for all seasons.

Top guest favorite

Apartment in New Ipswich

4.95 out of 5 average rating, 111 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.

Superhost

Apartment in Gardner

4.81 out of 5 average rating, 37 reviews

Main Street Sanctuary - Cozy, Whimsical Workspace

Cozy Urban Retreat: A snug studio with warm wood interiors and charming decor—your ideal spot to unwind or work in peace. Prime Location: Nestled on Main Street, stroll to tasty restaurants and quirky shops. Enjoy free parking and laundry steps away. Your Space: 300 sq ft studio with a comfy bed, sofa, desk, big walk-in closet, and private ensuite bath. Essentials: Mini-fridge, microwave, kettle, kitchenware, fresh linens, and easy keycode check-in await you.

Guest favorite

Guesthouse in Westminster

4.98 out of 5 average rating, 431 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!

Superhost

Barn in Holden

4.89 out of 5 average rating, 487 reviews

Farm stay in a Historic Ski Lodge turned Barn

Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the sheep and see the horses and chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.