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Holiday houses in Wellesley

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Wellesley

  • Total holiday rentals

    Explore 70 holiday rentals in Wellesley

  • Nightly prices starting at

    Wellesley holiday rentals start at $69 NZD per night before taxes and fees

  • Verified guest reviews

    Over 3,520 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Wellesley holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wellesley rentals

  • 4.8 Average rating

    Wellesley stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated holiday rentals in Wellesley

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

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Superhost
A cozy living room features a large sectional sofa and a coffee table on a patterned area rug. Natural light floods the space through sliding glass doors that lead to a lush backyard, enhancing the room's open feel. Decorative plants add a touch of greenery.
Home in Wellesley
4.71 out of 5 average rating, 17 reviews

Quiet Entire House 2Br/2Ba Walk to Train/Colleges

Entire 2 story colonial style 2Br single family in Wellesley Sq. The most convenient location in town! Easy access to Wellesley and Babson Colleges, walk to train to Boston, summer camps, Whole Foods grocery, restaurants. Large, lush fenced backyard with 2 Patios. Park/sports field/tennis courts/playground just beyond our backyard. Fast WiFi, free parking, AC/heating. 3 beds + mattress, office desks, 2 bathrooms, open concept living room & piano (upon request), TV, dining room, stocked kitchen.

Top Guest favourite
The exterior of a two-level home is depicted, surrounded by lush green lawns and mature trees. A pathway leads to the welcoming entrance, flanked by garden beds featuring various plants. The house features a traditional design with large windows allowing for ample natural light.
Home in Holliston
4.98 out of 5 average rating, 134 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 favourite
A charming farmhouse stands amidst a lush garden, surrounded by vibrant purple irises. The white exterior of the house contrasts beautifully with the greenery, providing a serene atmosphere. Tall trees and a manicured lawn enhance the inviting landscape of the property.
Guest suite in Weston
5 out of 5 average rating, 204 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 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

Top Guest favourite
Guest suite in Dover
4.98 out of 5 average rating, 332 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.

Top Guest favourite
A living area features a large wall adorned with natural-themed artwork, complemented by two windows allowing ample light. A flat-screen TV is mounted on the wall opposite a small table with a woven texture. A plush gray sofa enhances the inviting space.
Apartment in Newton
5 out of 5 average rating, 115 reviews

Inn at Newton Highlands, Suite 2, Apartment-Hotel

This gorgeous 1,800 sq. ft. 3 bedroom, 2 1/2 bathroom suite at The Inn at Newton Highlands is impeccably designed and decorated. It occupies the second and third floors of the building and immerses you in luxury and style. Its private 800 sq. ft. deck offers stunning views of the village. The space comes with a bonus room. This suite is one of several luxury suites in a small boutique Inn located in the heart of Newton Highlands in a beautiful , fully remodeled historic building.

Guest favourite
A cozy living area is presented with a comfortable gray sofa and a dark wooden coffee table. A small dining table with two chairs is positioned near the patio doors, which are flanked by light curtains. A patterned area rug adds warmth to the hardwood floor.
Apartment in Newton
4.93 out of 5 average rating, 405 reviews

Conveniently Located Private Garden Apartment

Garden-level apartment next to public park, yet convenient to Newton Centre, Chestnut Hill, Boston College, Longwood Medical Area, and public transit. Easy access to 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 enjoy the outdoors sitting on the patio. Come and go as you please with a private entry. Great for quick visits or extended stay. Newton Short Term Rental - STRA-23

Guest favourite
Home in Wayland
4.9 out of 5 average rating, 132 reviews

Spacious 4 bedroom home with large yard

Private and clean renovated 4 bedroom house in "Safest Town" in Massachusetts, 25 minutes from Boston. Perfect for families or travelers wanting extra space. Sleeps 8 comfortably in 4 bedrooms. Pets are completely welcome! Lots of walking trails nearby. Connected to another unit and shares the large backyard. Kids will enjoy the swingset. Lake Chochituate is near with canoe, kayak, and swimming. Close to MassPike, Rt.30 & 27, and many colleges and MetroWest office parks.

Top Guest favourite
A spacious living area features a vaulted ceiling, large windows allowing natural light, and a comfortable sofa. A wooden coffee table sits at the center, complemented by patterned armchairs. Adjacent, a farmhouse dining table accommodates six, enhancing the open layout.
Place to stay in Sherborn
4.98 out of 5 average rating, 352 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. NEW in 2022: Mini-split AC!

Top Guest favourite
A dining area with a dark wooden table is set for four, featuring a colorful table runner. Natural light filters through windows adorned with light curtains, illuminating a cozy living room space beyond, furnished with a sectional couch, decorative pillows, and houseplants.
Guest suite in Newton
4.95 out of 5 average rating, 152 reviews

New Markdown! Lovely 3 Bedroom Unit with Garage

Planning your World Cup trip? Boston host of 7 World Cup matches. Enjoy the comfort of a fully equipped home perfect for watching every game This beautiful sunlit second floor unit with private garage has 3 bedrooms, full bathroom, splendid modern kitchen, gracious dining room, an elegant living room and a dedicated pleasant office room . Enjoy the shared backyard with a patio and playground for the kids. Registration: STR - 24 - 12

Guest favourite
The living area is furnished with a soft sofa and decorative throw pillows, complemented by a patterned area rug. Natural light enters through sheer curtains, creating a bright and welcoming ambiance. A dining table with wooden chairs is visible in the adjoining space.
Home in Waltham
4.77 out of 5 average rating, 488 reviews

Beautiful, Clean & Quiet 2 BR- 15 min to BOSTON

SUNNY, CLEAN 2 bedroom with updated kitchen (granite counter top) and bathroom. Minutes to vibrant Moody Street for restaurants (great selection range from good old American food to Asian), local homemade ice cream shop, shops and a movie theater. Quiet, convenient location- 15 minutes to Boston and close to Brandeis University, Regis College, Bentley College and Lasell College. FREE PARKING, WiFi and WASHER & DRYER.

Top Guest favourite
A two-story white house features a welcoming front porch and black shutters. Lush greenery surrounds the property, with a well-kept lawn and flower beds. A pathway leads from the road to the entrance, and a driveway is visible beside the house.
Home in Dedham
4.98 out of 5 average rating, 296 reviews

Cozy, historic 3 bedroom home close to Boston!

Welcome to our cozy home. Our place blends historic charm with modern comfort. Enjoy a large, fenced yard with a grill, fire pit, and deck to relax. Inside, you'll find a well-equipped kitchen and a dining room. We offer three bedrooms with comfortable mattresses and soft bedding. The living room has a big TV with cable and streaming apps, plus high-speed Wi-Fi. Families with dogs are warmly welcomed.

Top Guest favourite
A comfortable living area features a sectional sofa in light gray, complemented by floral armchairs. A wooden armoire stands against the wall, while natural light floods in through large sliding doors leading to a deck outside. Bookshelves are visible in the background.
Loft in Natick
5 out of 5 average rating, 227 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.

Popular amenities for Wellesley holiday rentals

When is the best time to visit Wellesley?

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Avg. price$157 NZD$157 NZD$157 NZD$189 NZD$210 NZD$188 NZD$201 NZD$162 NZD$157 NZD$200 NZD$189 NZD$157 NZD
Avg. temp-3°C-2°C2°C8°C14°C19°C22°C22°C18°C11°C6°C0°C

Frequently Asked Questions

  • What are the best places to stay in Wellesley?

    Stays near the town center put guests close to dining, parks, and local events, while residential neighborhoods provide a quieter atmosphere. Many visitors select accommodations with access to green spaces and walking areas.

  • What are the best things to do in Wellesley with kids?

    Families can enjoy playgrounds, outdoor trails at local reservations, and interactive programs at town libraries. Seasonal events and public art are also engaging for younger travelers.

  • What are some of the best things to do in Wellesley?

    Explore walking paths at Elm Bank Reservation, visit public gardens, or tour local art spaces. The town also has coffee shops, boutique shopping, and seasonal farmers' markets for a taste of local life.

  • How is the weather in Wellesley?

    Wellesley has cold winters near 19–35°F (-7–2°C), with snow possible, and warm summers peaking at 63–82°F (17–28°C). Spring and fall bring changing foliage and milder temperatures, making outdoor activities comfortable.

  • When is the best time to visit Wellesley?

    Late spring and early autumn are often recommended for mild weather and vibrant natural scenery. Seasonal events, like outdoor concerts and festivals, typically take place during these periods.

  • What are the best places to visit in Wellesley?

    The Wellesley College Botanic Gardens, Elm Bank Reservation, and Davis Museum are often recommended. These sites showcase gardens, art, and the area's tranquil natural settings.

  • What are some hiking trails in Wellesley?

    Hikers explore the trails at Elm Bank Reservation, Morses Pond, and the Charles River Pathway. These routes showcase local woodlands, waterways, and the region's changing seasons.

  • What are some family activities we can do in Wellesley?

    Families can explore nature trails, picnic at public parks, and visit hands-on exhibits at local museums. Farmers' markets and seasonal festivals are also popular for group outings.

  • What are some of the best day trip ideas from Wellesley?

    Guests often explore nearby historic towns, coastal attractions, and cultural sites around greater Boston. Art museums, waterfront walks, and scenic parks are frequently suggested for day excursions.

  • Are there any pet friendly accommodations available in Wellesley?

    Several accommodations in Wellesley welcome pets, especially in residential and park-adjacent neighborhoods. Travelers may want to confirm pet policies and nearby walking areas in advance.

  • What are some local tips for visiting Wellesley?

    Bring comfortable shoes for exploring parks and campuses, and check town calendars for neighborhood events. Many visitors enjoy local farmer markets or public art installations during their stay.

  • What is Wellesley known for?

    Wellesley is known for its picturesque college campuses, abundant green spaces, and locally rooted community life. The town has a reputation for educational institutions and public gardens, drawing visitors who appreciate academic and outdoor experiences.

  • What are the best hidden gems to explore in Wellesley?

    Small sculpture gardens on college campuses, community art spaces, and quiet lakeside paths are sometimes overlooked. Morning visits to independent bakeries or galleries can reveal more of the town's local character.

  • What are the best foods to try in Wellesley?

    Wellesley has a diverse dining scene with fresh New England seafood, family-run bakeries, and international cuisines. Locally made pastries and artisanal coffee drinks are frequently suggested.

  • What should I bring for a trip to Wellesley?

    Pack layered clothing to adapt to changing New England weather, especially a light rain jacket and comfortable shoes for walking. If visiting in colder months, bring warm outerwear and hats.

  • What is the nightlife in Wellesley like?

    Wellesley has a relaxed nightlife scene focused on cozy cafes, pub-style restaurants, and occasional live music venues. For a wider selection of nightspots, many guests explore nearby urban areas.

  • What are the most popular events or festivals in Wellesley?

    Wellesley celebrates with an annual veterans' parade in late spring, outdoor summer concerts, and arts festivals during the warmer months. The town has community traditions that bring neighbors together throughout the year.

  • Are there family friendly vacation rentals in Wellesley?

    Many vacation rentals in Wellesley welcome families, with options that include multiple bedrooms, kitchens, and access to parks. Guests often find features that support family travel, including outdoor spaces or proximity to playgrounds.