Vacation rentals in Upton

Cozy Private 2 Bedroom Near Foxboro/Sleeps 5

Cozy private unit with 3 beds. Conveniently located near Gillette, with easy access to Boston, Providence and Worcester. Includes two bedrooms, a full kitchen, and a cozy living space with a sleeper sofa. Comfortable and thoughtfully updated, I have personally put so much love into this space to make it feel like a home away from home. This is a two family and the bottom floor is available for larger party bookings . Private entrance, WiFi, and parking included. Upstairs unit — stairs required

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.

Private Heaven with a Vineyard

Welcome to your private vineyard retreat in Wrentham. Set on over 6.8 acres at the end of a peaceful cul-de-sac, this charming escape offers a working vineyard, open fields, fruit trees, and private trails. Unwind by the cozy stove, entertain on the deck or patio with charcoal griller, and enjoy the screened gazebo with expansive field view. Perfect for nature lovers, families, or weekend getaways—just minutes from outlet mall, highway and local supermarket. Serenity, charm and comfort await.

2BR Private Suite Close to World Cup Sleeps 6

Welcome to your home away from home! This private, spacious two-bedroom guest suite spans the entire lower level of our home and features a private entrance, walk-out patio, full kitchen, laundry, and open living/dining area. Located just 26 minutes from Gillette Stadium/World Cup via an easy highway drive and in Hopkinton, the start of the Boston Marathon. It’s ideal for event travelers, runners, and families. Entry is through the main level and down one flight of stairs. Dog-friendly home.

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!

Beautiful & Historic New England Colonial c.1780

The Zadock Taft House is the quintessential historic New England post & beam colonial home & listed on the National Registry of Historic Places. The house is fully climate controlled and includes 3 bedrooms, a cozy “family parlor” providing a perfect to relax and watch tv, and our wonderfully restored “tea room” and “flower room!” We invite guests to step back in time while enjoying modern day amenities! Gillette Stadium-30min. Boston-50min. Providence-25min. Newport-60min. Worcester-25min.

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.

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

Welcome to our charming 3-bedroom lake cottage in Mendon, MA, where every sunrise paints the sky with breathtaking hues over tranquil waters. Accommodates 6 guests, making it ideal for families or couples seeking serenity. Enjoy lakeside coffee, fishing, kayaking, and evenings by the fire pit. We are pet-friendly, so feel free to bring your dogs along — if you have more than 1 dog, please let us know. Conveniently located near restaurants and attractions. Book now for a magical getaway!

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 Capacity: This is a 2-person suite.

The Outlaw's In-Law

Simple and cozy - a one-bed, walk-out basement in-law in an executive home on 10 acres of wildlife-filled wetlands. Private, off-street parking and 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 (25 mins to Gillette), a concert (30 mins to Xfinity/Great Woods), a ball game (15 mins to the train to Fenway), a quick road-trip stopover, or even a remote work-week!

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.

Clean & Cozy 2BR Across from Quinsigamond Lake

Unwind in our comfy 2-bedroom apartment with all the essentials for a comfortable stay. Work remotely while facing the lakeview. Super close to UMass Memorial, UMass campus, and just minutes away from Starbucks, Whole Foods, TraderJoe's and many more. Surrounded by many restaurants with great variety of taste. Easy access to the highway. Escape the ordinary and make this homy lakeview apartment your home away from home. Book now for a delightful experience!