Holiday houses in Upton

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Top-rated holiday rentals in Upton

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Top Guest favourite

Guest suite in Uxbridge

4.99 out of 5 average rating, 351 reviews

Beautiful, Unique, & Cozy Cedar Flat

Come enjoy this new and beautifully designed space in historic Uxbridge, MA. Set up like a tiny house, it is the most cozy and clean place you will visit. A ship’s ladder will take you to the queen loft bed or use a new PotteryBarn sleeper sofa. The Frame TV will act as a beautiful painting if you prefer to "unplug." Climate control and a hammock chair are a perfect combo! Located on a quiet street, it is an easy 25 min. drive to Providence or Worcester, and only 50 min. to downtown Boston.

Top Guest favourite

Farm stay in Thompson

4.99 out of 5 average rating, 190 reviews

Rustic Farmette Studio w/Pool & yearround Hot Tub

Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, or a family with a young kid. Please include all individuals (&pets) in your booking.

Top Guest favourite

Cabin in Thompson

4.99 out of 5 average rating, 126 reviews

Secluded cabin w/ Finnish Sauna & Forest Baths

A secluded, romantic, rustic, cabin alongside the French River - Frog Hollow is a perfect place to get away and experience the luxury of a wood fired sauna and forest baths. Located in the Quiet Corner of CT, relax as you watch the ducks, herons, turtles, and beavers along the river. Cook a delicious meal in the porch-enclosed kitchen, cozy up next to the woodstove fireplace, work remotely with a water view, or go for a paddle on the river. Ideal for a couple or solo traveler wanting to unwind.

Top Guest favourite

Guest suite in Uxbridge

4.97 out of 5 average rating, 191 reviews

The 1780 Suite

Join us for a step back in time at our unique bucolic property. Set on a scenic road, the post and beam farmhouse was built in 1780 and offers a haven of peace and tranquillity after a busy day of exploring New England. Guests have a private entrance and wind their way up the period staircase to the second-floor suite with two bedrooms, a sitting room, a breakfast nook, and a bathroom. Enjoy your morning coffee outside on the Adirondack chairs as you contemplate the charms of country living.

Guest favourite

Guest suite in Franklin

4.89 out of 5 average rating, 165 reviews

Cozy, Cute & Charming In-Law Apt w/Private Access

Cozy, Cute & Charming In-Law Apt w/ Private Access & Parking in Franklin City Center. Everything is within walking distance. It’s perfect for couples, solo adventures and business travelers. Just minutes walk to Train Station, Shopping Centers, Restaurants, Museum, Theater House, Libraries, Dean College, Trail & Tracking. Few minutes drive to Gillette Stadium, Wrentham Outlets, Xfinity Center, Boston Marathon Starting Point. You can easily visit Boston, Providence, Newport & Worcester, too!

Top Guest favourite

Home in Scituate

4.98 out of 5 average rating, 146 reviews

Artist studio in the woods

Take it easy at this unique and tranquil getaway. Be a little bohemian, stay in an artist’s studio for two adults, views of woods and stone walls.walk along a 300 stone wall past a 5000 gallon koi pond, and discover a stone sculpture in the woods. Wall of windows, private deck, queen size bed, kitchenette, full bath, dishwasher, Wi-Fi, cable tv, guest robes, iron and board, kuerig, all necessary utensils. Quite, tranquil, relax. Pool has surcharge $20 if weather is good during your stay.

Top Guest favourite

Tiny home in Greenville

4.97 out of 5 average rating, 708 reviews

Tiny Home Eco-Cottage w/ Lake View + Pet Friendly

Good things definitely come in pet friendly, environmentally conscious, small packages. Solar upgrade makes this lake front cottage 100% energy efficient. Built with an open, thoughtful design offering private bath, washer/dryer, full kitchen, Hotel Suite Luxury bedding and Tempur-Pedic mattress, blazing fast wifi, 46"HDTV (w/ Netflix, Sling, Prime and Plex), private deck with nice lake view. Cozy, charming and stocked with everything you could want for a perfect vacation or staycation.

Guest favourite

Campervan/RV in Millville

4.91 out of 5 average rating, 228 reviews

Vintage Americana style camping - 1950 Spartanette

If you enjoy CAMPING, you will love sleeping in a vintage camper! It's springtime, the birds are singing and the peepers are peeping. Come cozy up at the fire pit to a warm campfire and roast marshmallows. We provide plenty of firewood to build a nice campfire. The camper is safely located on our property and has beautiful views of the woods. Plenty of fresh drinking water is provided. Queen bed. NO SHOWER or Running water. Portable toilet. Heat. Grill. WIFI spotty while in the camper.

Top Guest favourite

Guest suite in Uxbridge

5 out of 5 average rating, 240 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.

Guest favourite

Guest suite in Marlborough

4.87 out of 5 average rating, 286 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 favourite

Treehouse in Willington

4.91 out of 5 average rating, 445 reviews

Treehouse - Countryside - Farm Animals - Fire Pit

Top Guest favourite

Guesthouse in Framingham

4.97 out of 5 average rating, 282 reviews

Private guest house on beautiful country road

Welcome to Grove Street Studio - our detached guest house which sits right behind our home on one of the most beautiful streets in the area. This two-room studio has everything you need for a comfortable stay including your own deck looking out to the woods behind. Perfect for for a hotel alternative for someone working temporarily at nearby businesses.

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Other great holiday rentals in Upton

Superhost

Private room in Southborough

4.89 out of 5 average rating, 122 reviews

Room with full bath, Queen bed

AlexRating, 5 stars3 weeks ago

Brilliant! Amazing stay, a very lovely family, very comfortable, clean, felt right at home! I would highly recommend! I was mindful of the quiet hours and their check-in/check-out instructions were easy to follow! They were very nice!!

Guest favourite

Guesthouse in Shrewsbury

4.89 out of 5 average rating, 9 reviews

New Private Apartment

MadeleineRating, 5 stars1 month ago

Super beautiful and peaceful for our entire stay! I loved it! :)

Guest favourite

Private room in Northborough

4.95 out of 5 average rating, 159 reviews

Swan Home with warm vibes - Guest BR & Pvt Bath

AnithaRating, 5 stars1 week ago

Mena was very nice, the room was spacious and clean and the house was in a beautiful location on the lake. Easy access to the town. Would stay again.

Guest favourite

Apartment in Worcester

5 out of 5 average rating, 12 reviews

Newly Refreshed 3bd Spacious Unit Minutes from 290

WilfreRating, 5 stars2 weeks ago

Would stay here again, one of the best in Worcester

Top Guest favourite

Private room in Westborough

4.98 out of 5 average rating, 749 reviews

Elegant Rooms in My Antique Home

MattRating, 5 stars4 weeks ago

An awesome place for us to stay after moving to Worcester! Cute and comfortable. Philomena was incredibly responsive and accommodating for our late check-in. Extremely comfortable & private accommodations.

Guest favourite

Private room in Uxbridge

4.88 out of 5 average rating, 132 reviews

Private Guest Suite in quiet area

ScottRating, 5 stars2 days ago

Cute comfy spot, felt like home. Super clean and tidy

Top Guest favourite

Private room in Northbridge

4.98 out of 5 average rating, 202 reviews

Coastal-themed B/R In A Quiet & Cozy Country Home

BrankoRating, 5 stars2 days ago

Dave and Chelsea were wonderful and gracious hosts. The bedroom was exactly as described. Location was very quiet for a good nights rest. Wonderful hosts.

Guest favourite