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Vacation rentals in Upton

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Upton

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

Guest favorite

Guest suite in Uxbridge

5.0 out of 5 average rating, 267 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.

Apr 29 – May 6

R2,740 ZAR per night
Guest favorite

Guest suite in Thompson

4.98 out of 5 average rating, 112 reviews

Meadowside: Perfect Location w/ Endless Recreation

Perfect location, great value, & tons of privacy! Come stay at Meadowside! You'll be in a beautifully appointed and completely private 620 sq ft in-law suite. We're a quarter mile away from Webster Lake and an easy drive to all area attractions! Bring your boat, as we have plenty of room for your trailer in our parking lot-sized driveway! Room to sleep up to 4, king bed in the master, 1.5 baths, kitchen, laundry, front farmer's porch, and garden dining! You name it, it's here at Meadowside!

Aug 19 – 26

R2,818 ZAR per night
Guest favorite

Guesthouse in Uxbridge

5.0 out of 5 average rating, 117 reviews

Zen Inspired Private Suite with 2-mile Trail Loop

Zig-Zag Trails unique offering is a harmonious blend of modern comfort and the timeless allure of rural living. A newly built 1000 sq ft guest suite situated on over 65 acres of private meadows and forests with zig-zagging trails throughout, providing the ultimate getaway to relax and recharge. This property is a haven for nature lovers and homebodies alike. We are conveniently located in the heart of the Blackstone Valley, 1hr from Boston, 35min from Providence, and 25min from Worcester.

Nov 19 – 26

R3,056 ZAR per night

Popular amenities for Upton vacation rentals

Stay near Upton's top sights

Red Rock Grill and Bar7 locals recommend
Shaw's4 locals recommend
Price Chopper3 locals recommend

Other great vacation rentals in Upton

Guest favorite

Barn in Holden

4.9 out of 5 average rating, 375 reviews

Farm stay in a Historic Ski Lodge turned Barn

Jun 10 – 17

R3,482 ZAR per night
Guest favorite

Guest suite in Littleton

4.91 out of 5 average rating, 309 reviews

Historic Loft with bathroom & kitchenette

Jul 25 – Aug 1

R2,003 ZAR per night
Superhost

Cottage in Scituate

4.9 out of 5 average rating, 193 reviews

5 Star cottage in historical Clayville

Jul 13 – 20

R2,346 ZAR per night
Guest favorite

Apartment in Dudley

4.82 out of 5 average rating, 348 reviews

웃❤️유 PRIVATE STUDIO - SAFE GORGEOUS HIDEOUT

Dec 4 – 11

R1,575 ZAR per night
Guest favorite

Guesthouse in Westminster

4.98 out of 5 average rating, 286 reviews

Guest House - 4 miles from Wachusett Mt.

Jun 18 – 25

R2,605 ZAR per night
Guest favorite

Farm stay in Thompson

4.94 out of 5 average rating, 152 reviews

Wizard's Roost and Underhill Hollow

Oct 20 – 27

R2,176 ZAR per night
Guest favorite

Cottage in Petersham

4.99 out of 5 average rating, 146 reviews

Cider House Cottage

Nov 6 – 13

R2,621 ZAR per night
Guest favorite

Guest suite in Warren

4.95 out of 5 average rating, 263 reviews

Craig's Cove

Jun 25 – Jul 2

R1,355 ZAR per night
Guest favorite

Cottage in Worcester

4.86 out of 5 average rating, 103 reviews

Unique and Private Cottage in Worcester

Feb 10 – 17

R2,598 ZAR per night
Superhost

Apartment in Hopkinton

4.82 out of 5 average rating, 28 reviews

Cute family getaway near Boston

May 5 – 12

R2,220 ZAR per night
Guest favorite

Apartment in Sutton

4.81 out of 5 average rating, 52 reviews

Spacious, 1 bedroom, full kitchen and laundry.

Jan 5 – 12

R1,744 ZAR per night
Guest favorite

Cottage in Southborough

4.96 out of 5 average rating, 25 reviews

Willow Creek Cottage

Oct 28 – Nov 4

R2,372 ZAR per night

Destinations to explore

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  5. Upton