Holiday rentals in Southborough

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Top-rated holiday rentals in Southborough

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

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Guest favourite

Flat in Framingham

4.92 out of 5 average rating, 259 reviews

Spacious 2 Br with All The Comforts Of Home

This a quaint apartment . Not your typical hotel room. In a country setting but 5-10 minutes from great shopping, restaurants, parks, colleges and major highways. Boston is 22.5 miles away. Fenway Park is 20 miles. Worcester is 17 miles. Private location overlooking conservation land. Walk to great hiking and biking trails but car needed for other activities. Full kitchen, laundry room and living room in addition to 2 br and bath. It has the comfort of a home away from home. Please NO PETS.

13–20 Dec

$211 SGD per night

Guest favourite

Home in Southborough

4.91 out of 5 average rating, 137 reviews

Luxury Living at its Best in X-Large 8 Beds Estate

The talk & admiration of the neighborhood. Airbnb Guests’ Favorite with over 130+ 5 Star Reviews. When you book, we aim to deliver everything that is described in order to earn the same 5 stars all around review from you. This large expansive 8 bedrooms, 4.5 baths estate home has had a complete renovation adding today’s high end touches, yet preserving old world charm. You will experience modern amenities, a massive kitchen & luxury living in a large open space. SORRY: We do not allow parties.

26 Dec – 2 Jan

$724 SGD per night

Guest favourite

Home in Framingham

4.89 out of 5 average rating, 246 reviews

1BR—Bright & Cozy 2-Level Home — 25 Min to Boston

750sqft One-Bedroom, 2-Level Apartment @ our 3-Rental Property 1st Floor: —Fully Stocked Granite Kitchen w/Dishwasher + Essentials & Cookware —Living Room w/Queen Sofa Bed & Dining Table 2nd Floor: —Bedroom - Queen Memory Foam Bed + Full Length Mirror —Bathroom - Shower/Tub —Desk & Chair + Wardrobe Backyard Patio Laundry Room (Basement) Driveway Parking 25 min to Boston 15 min walk to Train 5 min walk to Jack’s Abby Brewery 3 min walk to Park/Playground Cleaned & Sanitized/COVID Conscious Host

29 May – 5 Jun

$255 SGD per night

Guest favourite

Guest suite in Uxbridge

5.0 out of 5 average rating, 126 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.

31 Aug – 7 Sep

$218 SGD per night

Guest favourite

Guest suite in Littleton

4.91 out of 5 average rating, 315 reviews

Historic Loft with bathroom & kitchenette

A beautiful 1840s barn loft steps away from miles of hiking trails. Fully separate and private entrance, bathroom, and kitchenette. Enjoy a serene, rustic cabin atmosphere with a historic brick hearth and exposed beams. Southeast facing windows overlook patio, garden and ruins. Off the beaten path but only 5 min. to Rte 2, Rte 495, and Boston commuter rail. Drive times w/o traffic: 45 min. Boston, 20 min. Lowell/ Rte 3, Burlington, Bedford, Nashua 30 min.

13–20 Sep

$143 SGD per night

Superhost

Home in Shrewsbury

4.85 out of 5 average rating, 197 reviews

A Fabulous House with Beautiful Views

Gorgeous home with spectacular views and sunset! This big house overlooks the rolling Worcester hills for miles and miles. Convenient location, quiet neighborhood, big backyard, expansive deck, and nearby scenic hiking trails. The house has 3 bedrooms, 1 kitchen, 3.5 bathrooms, washer & dryer, enclosed porch, and lots of parking space. Great place for large group gatherings. Beautiful and comfortable, with everything you'd need for cooking and relaxing.

1–8 Aug

$191 SGD per night

Guest favourite

Flat in Framingham

4.95 out of 5 average rating, 184 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

24–31 Jul

$140 SGD per night

Guest favourite

Flat in Hudson

4.85 out of 5 average rating, 294 reviews

Private Mother-In-Law apartment on the lake!

Waterfront on the Lake with a private beach and dock. Relax on your deck and Patio with Wonderful Views. This is a mother-in-law private downstairs apartment complete with kitchen and separate entrance. Enjoy the lake with a fire pit and use of paddle boat and kayaks (life jackets provided). Enjoy the wonderful eclectic restaurants in downtown Hudson including a Micro Brewery, Pub, Martini Bar, Micro Creamery and even a SpeakEasy.

14–21 Sep

$124 SGD per night

Guest favourite

Flat in Hudson

4.92 out of 5 average rating, 429 reviews

Newly Renovated Apartment Near Downtown Hudson

Newly renovated private attic apartment near downtown Hudson with kitchenette, living room and bedroom/office. A warm, cozy space with plenty of natural light! Just upgraded to a new king sized bed! Free parking on site Walking distance to restaurants, cleaners, antique shops, roller skating, shopping center, gym, breweries, golf course... & lots more! Nearby there are lots of historical sites, ski areas, and areas for swimming!

19–26 Sep

$186 SGD per night

Guest favourite

Guest suite in Marlborough

4.88 out of 5 average rating, 252 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!

7–14 Jan

$92 SGD per night

Guest favourite

Guest house in Framingham

4.98 out of 5 average rating, 203 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.

2–9 Apr

$161 SGD per night

Guest favourite

Flat in Natick

4.98 out of 5 average rating, 333 reviews

Scandi-Modern Apartment

Charming walk-out ground level apartment in a quiet residential neighborhood. Conveniently located west of Boston with easy access to highways. Walkable to grocery store, pharmacy, banks and restaurants. Walk the nearby trail to Lake Cochituate and the Cochituate Rail Trail is less than 1 mile away. Natick Mall is 1.3 miles. EV charging available.

24–31 Oct

$171 SGD per night