Vacation rentals in Upton

All New Private Country Setting (2 Level-No Share)

We built this 2 level home 6 years ago and it is located on Washington St in the towns Historic district. The home is set back from street with a long country style driveway. We designed it with large windows in all rooms, welcoming the sunlight and peaceful setting. Access to clean and empty garage for storage (No parking). We have no personal items in the guest level - all closets and dressers are empty and yours for full use! Co Host reside in lower separate entrance suite. Nothing Shared.

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.

2-Bedroom in Hopkinton-home of the Boston Marathon

Welcome to your home away from home! This spacious "in-law apartment" spans the entire lower level of our home , with a private entrance and walk-out patio. Features include two bedrooms with Tempur-Pedic beds, a sunny king-size primary, full kitchen, laundry, and open living/dining area — perfect for relaxing, working remotely, or gathering with family. You'll enter on the main level and the apartment is down a flight of stairs. This is a dog-friendly home - you'll see him in the backyard.

Cute family getaway near Boston

Have fun with the whole family at this stylish newly built apartment. In the apartment - a bedroom, a TV-room that can be converted to a bedroom (with a convertible Sofa Bed), dining/working space, kitchen. Full bath. The apartment is about a 2 miles from the Hopkinton marathon start line, and has access to a supermarket and restaurants within walking distance. Boston Airport and Boston downtown are about 35 minutes drive (without traffic). If you need, laundry is available on premises.

Entire Historic Carriage House with Fireplace & AC

Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

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.

Centrally Located Apartment in Worcester

This first-floor unit in a charming 1910 duplex offers modern comfort and unbeatable convenience. Located within half a mile of Worcester State University and a grocery store, and within walking distance of restaurants and shops, it’s perfect for any lifestyle. The updated space features lightning-fast 1 Gbps WiFi, two workspaces, off-street parking for one car, and plenty of on-street parking. Ideal for both work and relaxation, this home is fully equipped for a comfortable stay.

Exquisite 1 Bedroom Suite-Charming,W/Private Entry

An exquisite and convenient I BR Modern suite nestled between Boston and Worcester is available for you. Bright and charm w/ a . Beautiful kitchen, remodeled bathroom and a bedroom. Private entrance w/ it’s lovely courtyard to sit outdoor, a free parking spot/ WiFi. The apartment is conveniently located to Babson and Wellesley College, both within 7 miles , FSU is 1 mile train station 2 miles , easy drive to Cape Cod. For all travelers & enjoy your stay her !

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.

Tranquil studio suite

Experience the blend of simplicity and sophistication in this brand-new apartment, complete with essential appliances and stylish furnishings. Nestled in a tranquil wooded area, you'll enjoy easy access to highways, charming coffee shops, and the most beautiful nature walks. This basement studio apartment offers all the essentials while ensuring plenty of privacy. 2 mins to 146 highway 25 mins to Worcester 30 mins to Providence 1 hour to Boston

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!

The Outlaw's In-Law

Simple and cozy - this single-bed, walk-out basement in-law is part of an executive home on 10 acres of wildlife-filled wetlands. It includes private, off-street parking and has very convenient access to major highways, shopping, eating, and entertainment, whether you're visiting for business or pleasure! Perfect if you're in town for the big game, a concert, a a quick road-trip stopover, or a remote work-week!