Holiday houses in Wellesley

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Top-rated holiday rentals in Wellesley

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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

1 – 8 May

$1,960 AUD total

Guest favourite

Guest suite in Weston

5.0 out of 5 average rating, 115 reviews

FLOWER FARM GETAWAY 2BR 15MIN TO BOSTON

Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 15 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.

28 Oct – 4 Nov

$2,704 AUD total

Guest favourite

Apartment in Newton

4.95 out of 5 average rating, 147 reviews

Sunny, private, comfortable 1 bedroom-convenient.

This listing features a sunny great room. The great room has a large, comfortable couch, TV and desk. Highlights include a modern kitchenette, a new bathroom and air mattress available upon request. The bed is FULL size. You'll have a private stairway that leads to your private entrance. Nice view for sunsets. You have a dedicated parking space. The apartment is in Newton Upper Falls. Close to Mass Pike, route 128 and route 9. It is a 15 minute walk to the Green Line -D route-Eliot Stop

9 – 16 Dec

$1,992 AUD total

Guest favourite

Guest suite in Wellesley

4.98 out of 5 average rating, 211 reviews

Spacious Private Entrance Master Bedroom/Bath

Private entrance master bedroom w/exclusive use of attached master bathroom. Studio apartment-like room w/private exterior staircase entrance. Walk to Wellesley College, town center, commuter rail, restaurants, stores, Whole Foods. Short drive to Babson. Sizable room, tasteful decor, king bed, sitting area, microwave, fridge (no TV). High-speed wifi, deck, situated amongst the treetops. Safe suburban neighborhood. Walk/jog trails, tennis courts, walk to spa/gym/yoga w/reasonable day fees.

8 – 15 Feb

$1,877 AUD total

Guest favourite

Apartment in Newton

4.91 out of 5 average rating, 265 reviews

Conveniently Located Private Garden Apartment

Garden-level apartment next to a public park yet convenient to Newton Centre, Chestnut Hill, and public transportation. Easy to take in all the Boston area attractions. Sleep late in a comfy bedroom with blackout shades, relax in front of the 55" HDTV, whip up a quick meal in the kitchenette, or sit on the patio and enjoy the outdoors. Come and go as you please with a private entry. Great for quick visits or extended stays. Please note: Construction next door can be loud during the day.

20 – 27 Sept

$2,089 AUD total

Guest favourite

Guest suite in Sherborn

4.97 out of 5 average rating, 239 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!

6 – 13 June

$2,066 AUD total

Guest favourite

Guest suite in Dover

4.98 out of 5 average rating, 182 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-stairs climbing required to reach bedroom suite.) I welcome quiet, mature guests. 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, and surprisingly close to downtown Boston. I have owned and loved this home for 33 years and take great joy in its charm and outdoor spaces.

26 Feb – 5 Mar

$1,790 AUD total

Guest favourite

Apartment in Hudson

4.85 out of 5 average rating, 292 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.

20 – 27 Sept

$1,122 AUD total

Guest favourite

Apartment in Newton

4.96 out of 5 average rating, 381 reviews

Sunny apartment in gracious Victorian

Relax into your Boston stay! We offer a sunny in-law apartment on the first floor of a gracious owner-occupied Victorian house. Quiet, safe residential neighborhood. Private entrance. Spacious bedroom, living room with sofabed, kitchenette & bath. Strong Wi-fi. Driveway parking. Contactless check-in, Easy access to Boston, Cambridge, Rts. 128 & 90, and Charles River bike path. Let us welcome you!

4 – 11 July

$2,044 AUD total

Guest favourite

Guesthouse in Framingham

4.97 out of 5 average rating, 199 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.

25 Feb – 4 Mar

$1,419 AUD total

Guest favourite

Apartment in Natick

4.98 out of 5 average rating, 331 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.

29 Sept – 6 Oct

$1,611 AUD total

Guest favourite

Loft in Natick

4.99 out of 5 average rating, 174 reviews

Lakeside Studio Loft

Bright, open, private 900 sq foot loft space on Lake Cochituate. This is a mother-in-law suite attached to our lakeside home. This airy studio includes a queen bed, kitchen (no stove or oven) toaster,microwave,hot plate and George Foreman grill, skylit bathroom, living room with television and lakeview deck.

9 – 16 Mar

$1,802 AUD total