Vacation rentals in Sherborn

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Top-rated vacation rentals in Sherborn

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Top guest favorite

Home in Holliston

4.97 out of 5 average rating, 97 reviews

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.

Top guest favorite

Guest suite in Weston

4.99 out of 5 average rating, 169 reviews

Flower Farm Getaway 2BR, 20 Min To Boston

Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 15-minute drive to Amtrak's "Route 128" station to NYC and points south.

Top guest favorite

Apartment in Wayland

5 out of 5 average rating, 22 reviews

Cozy lakeside retreat

Take it easy at this unique and tranquil getaway a perfect spot to recharge and enjoy all Dudley Pond has to offer.Relax on the deck overlooking the water OR explore on a canoe, kayak, or paddleboard OR walk to TheChat (an old speakeasy) for yummy drinks and food. Centrally located in the Metrowest suburbs close to the Mass turnpike and public transportation to downtown Boston. Close to Babson, Wellesley College, Boston University, Brandeis, Framingham State for graduation or parent weekends.

Top guest favorite

Guest suite in Dover

4.97 out of 5 average rating, 280 reviews

Peaceful Country Home, Dover, Ma: Private Entrance

Graceful country oasis in a renovated 125 year old historic home, 35 minutes driving time from downtown Boston. (Important-stair climbing required to reach bedroom suite.) I welcome quiet, mature guests as this is a very peaceful (non-party)environment. We are located on a scenic road in sophisticated Dover, Ma, a commuter/country setting, with miles of hiking trails and roads ideal for cycling. I have owned and loved this home for 35 years and take great joy in its charm and outdoor spaces.

Superhost

Guest suite in Wellesley

4.65 out of 5 average rating, 215 reviews

Cozy Garden Suite | EV Charger + Private Entry

Experience comfort in this ground-level in-law suite, located in a historic home in the heart of Wellesley, a charming college town just outside Boston. The kitchenette has a fridge, microwave, toaster, and other essentials for light meals, and a cozy atmosphere for relaxing or working. Close to Babson, Olin, and Wellesley College, it’s perfect for students, visiting faculty, or anyone seeking a peaceful short- or long-term stay. Single occupancy preferred. There is a charge for extra guests.

Guest favorite

Guest suite in Franklin

4.89 out of 5 average rating, 170 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 favorite

Place to stay in Sherborn

4.97 out of 5 average rating, 306 reviews

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!

Top guest favorite

Home in Framingham

5 out of 5 average rating, 29 reviews

1BR—Peaceful Guest House w/HotTub—20 Min to Boston

Welcome to our Guest House! 100% Private 1-Bedroom Place We Live In/Rent Main House (Details Below — See ⭐️) Queen Bed—New Memory Foam Mattress Fully Stocked Kitchen—Utensils, Pots/Pans & Essentials Dining Area—Table & Chairs Living Room—Leather Recliner Sofa Bathroom—Plush Towels & Natural Products 43” SmartTV—Netflix+Sling Live TV Private Porch & Private Entrance w/Keypad Hot Tub—On Our Deck Complementary Laundry Service Quiet Neighborhood 20 Mins to Boston Cleaned & Sanitized

Top guest favorite

Guest suite in Uxbridge

5 out of 5 average rating, 254 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.

Superhost

Guest suite in Framingham

4.84 out of 5 average rating, 81 reviews

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 !

Top guest favorite

Apartment in Framingham

4.96 out of 5 average rating, 282 reviews

Comfortable apartment in Framingham

Newly renovated basement apartment. Private entrance and living space which includes a kitchen, bedroom, hallway and bathroom. The kitchen has a microwave and refrigerator, but no stove. Very clean and well maintained. Comfortable queen size bed. Driveway space for 1 car and plenty of street parking. Great location. Walking distance to Dunkin' Donuts, Domino's Pizza, and local shops. Less than 2 miles from the Mass Pike. No Pets / No Smoking inside

Guest favorite

Apartment in Holliston

4.96 out of 5 average rating, 123 reviews

Lake Link

Beautiful fully stocked 2 BR apartment located in Holliston Historic District. Top of the line swimming pool with waterfall and hottub (May 31-Sep 30). Full kitchen, full bath, washer/dryer, central heat and AC, fireplace, wireless internet, Cable TV with almost all premium channels available, private driveway and entrance. Sorry, but no pets allowed. Note: COVID19- We require all eligible guests to be vaccinated or have 72 hr negative test.