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House vacation rentals in Wellesley

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Top-rated house rentals in Wellesley

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Top guest favorite

A warm living area features a brown leather sofa accompanied by two striped chairs. A rustic table stands in the center, while a colorful area rug covers the floor. An artwork hangs on the wall, and a 'Boston' sign adds character to the space.

Home in West Roxbury

4.99 out of 5 average rating, 268 reviews

The Red Door Carriage House

The Red Door Carriage house is a historic 90 year-old structure that was the carriage house for the original farmhouse (our home) on the property. Located in beautiful West Roxbury Mass., the unit is 3 miles from Fenway (Red Sox), Longwood Medical Center (all of the major hospitals) and 2 miles from Boston College. A 5 minute walk to the West Roxbury commuter rail station (10 minutes to South Station) and all bus lines into Boston, this apartment is a spectacular private and tranquil retreat.

A welcoming entryway showcases a wooden staircase leading to the upper levels. The space is enhanced by decorative topiary arrangements and features light-colored flooring providing a bright ambiance. Natural light emanates from a nearby doorway, revealing glimpses of the outdoor area.

Home in Stoughton

4.95 out of 5 average rating, 124 reviews

Modern home 22 min Boston, 20 min Gillette Stadium

Experience New England charm in this luxury home, with over 3,500 sq. feet of living space. This home has many unique characteristics that includes a Koi pond, a majestic backyard and an indoor sauna to make your short term or long term stay more comfortable. It's located in a quiet neighborhood that is walking distance to Glen Echo Park, where hiking, and fishing is available. It's 2 min away from shops, major highways, and has a 6-car driveway and unlimited on-street parking. Pet friendly!

A stone fireplace is framed by a slate hearth and topped with a white shelf displaying framed photographs. Adjacent, a small black table stands with a decorative plant. Light wood flooring extends into the background, leading to a room with a radiator and a sideboard.

4.93 out of 5 average rating, 114 reviews

Cozy house close to Boston

My home is very comfortable with a casual feel. I have three bedrooms with 1.5 bathrooms. I have two queen size beds and one twin size bed. My kitchen and bathrooms are updated. I have a cozy den with a Smart TV and a living room that is a comfortable place to relax. The outdoor area has a deck leading onto a patio with a fire pit. I have an outdoor gas grill. It's a great place to unwind and relax. It is fenced in with privacy. I also have a driveway and on street parking is available.

Top guest favorite

The kitchen features a modern layout with white cabinets and granite countertops. Stainless steel appliances, including a French door refrigerator, are complemented by a tiled backsplash. Natural light enters through multiple windows, illuminating the spacious area. Two area rugs add warmth to the tiled floor.

Home in Framingham

4.98 out of 5 average rating, 249 reviews

2BR—Lovely 1900s Home—1200sqft—25 Min to Boston

Welcome to our Charming 1900s House! 1200sqft 2nd/Top Floor Private Apartment @ our 3-Rental Property **Children 10+ Welcome** Granite Kitchen w/ Dishwasher - Fully Equipped w/ Essentials & Cookware Tiled Bathroom w/ Bathtub & Shower 2 Queen Bedrooms 2 Desks & Chairs Reclining Sofa & Glider Loveseat Laundry Room (Basement) Patio & Grill Driveway Parking—2 Spaces Private Entrance 25 Min Drive to Boston 15 Min Walk to Train 5 Min Walk to Jack's Abby 3 Min Walk to Park Deep Cleaned & Sanitized

A welcoming living area features a gray sofa and a green couch, complemented by a patterned area rug. A television sits on a stand against the wall, while indoor plants add a touch of greenery. Natural light illuminates the space from well-placed ceiling lights.

Home in Newtonville

4.95 out of 5 average rating, 133 reviews

Newly Renovated Lovely 2 bedroom unit - Newton MA

Only a 10 minute drive to the heart of Boston's downtown area and other central Boston colleges and universities. This is a newly renovated 2 bedroom unit with 2 bathrooms on the first floor for parties up to 7 people (convertable couches) in a quiet and peaceful Irish suburban community. Driveway and street parking is always available. About an 11 minute walk to the nearest commuter rail line. Laundry access in the basement. No indoor smoke and no open flames, fines will be issued if caught.

A cozy living room is highlighted by wood paneling and exposed beams. Plush seating includes a sofa and two armchairs. A coffee table is centered in the space, with a television displaying programming. Natural light fills the room through multiple windows adorned with soft curtains.

Home in Brighton

4.93 out of 5 average rating, 337 reviews

All the comforts of home, quiet city neighborhood

Sleep peacefully in this beautiful home above Oak Square>Brighton>Boston. Updated, comfortably furnished, well-stocked with electronics, appliances, and housewares. Driveway parking spot. Ideal for couples, solo adventurers, and business travelers with auto or use ride services. Laundry service one mile away. Newbury Street: 8 miles away, North End: 9 miles, Seaport: 9 miles, Logan airport: 11 miles. Close to BC/Harvard; 1 mile from I-90/Mass Pike in Newton Corner, restaurants, attractions.

Top guest favorite

The living room features two dark leather sofas arranged around a circular glass coffee table. Natural light enters through large windows adorned with light-colored drapes. A mirror on the wall complements the warm beige walls, enhancing the space's cozy atmosphere.

Home in Wayland

4.92 out of 5 average rating, 157 reviews

Quiet & Cozy 4 BR in Metrowest- 25 mins to Boston

Keep it simple at this peaceful and centrally-located home. Cozy, quiet & clean 4 bedroom and 2 bathroom home conveniently located in the Metrowest area- 25 minutes to Boston. Situated in a very quiet neighborhood, close to grocery stores, restaurants and shopping. Guests will have access to the entire home excluding the garage. * Free parking * Free high speed internet/WiFi * Premium Cable channels * Basic cookware & dinnerware * Access to free Washer & Dryer * Keypad Entry System

The exterior of a two-family home is presented, featuring a dark wooden facade and a welcoming porch. Lush greenery, including flowering shrubs and trees, frames the entrance. A stone path leads to the front door, while neatly arranged plants add a touch of natural beauty.

Home in Harvard Square

4.93 out of 5 average rating, 268 reviews

Harvard Square - free permitted on street parking

WE NOW HAVE VERY FAST INTERNET SERVICE! Located in Harvard Square, minutes away from HARVARD ,HARVARD LAW, and HARVARD BUSINESS SCHOOL The two bedroom home has two large living rooms with books and original art. An easy walk to reach two excellent cafe's or visit the Harvard Art Museum to see a Van Gogh or Cezanne or have a fabulous meal. *Also, this apartment is not owned by an investment firm or controlled by a property management company.

A modern kitchen features a central wooden island with a gas stove and a griddle, surrounded by fresh produce. The space includes a dining table with wooden chairs and is adorned with colorful art on the walls, illuminated by natural light from large windows.

Home in Brookline

4.92 out of 5 average rating, 134 reviews

Pretzel Factory Loft w/Peloton

Creative loft style house that is home to a fashion designer and her family! Two floor loft like living very centrally located in Brookline MA. Very centrally located in Brookline Village. A few minutes walk to the T and very close to the hospital district. Whole house perfect for the whole family with fast Wifi and garage parking. Search for 'Everywhere Architecture' & click on 'White Place' to see more pictures!

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 West Newton

4.77 out of 5 average rating, 441 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 favorite

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.

4.98 out of 5 average rating, 254 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.

A dining area is shown with a long wooden table set with neutral placemats. Four tan chairs surround the table, and a decorative flower arrangement is placed at its center. Natural light filters through three large windows, framed by soft gray shades.

Home in West Newton

4.91 out of 5 average rating, 163 reviews

Convenient 2BR Condo W/Private Parking in Newton

This is a duplex condo that can comfortably accommodate two families. The upper level has 2 bedrooms and 1.5 bathrooms, suitable for 2–4 guests. The lower level (basement) has 1 bedroom and 1 bathroom, also suitable for 2–4 guests. If you would like to use the basement space, please let us know in advance. The basement suite will be opened for group of 6 guests or more.

Vacation rentals for every style

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Popular amenities for Wellesley house rentals

Free parking on premises

Air conditioning

House rentals with a pool

A vibrant garden is visible, featuring a variety of colorful flowers, including pink roses and white blooms. A white picket fence lines the path, complemented by lush greenery and tall trees in the background, creating a serene and inviting atmosphere.

Home in North Andover

4.94 out of 5 average rating, 167 reviews

Nana-tucket Inn

Top guest favorite

A private heated pool is surrounded by lush greenery, providing a tranquil setting. Loungers are positioned nearby, and a blue lane divider is visible across the pool. Sunlight reflects off the water, enhancing the serene atmosphere.

5 out of 5 average rating, 25 reviews

Villa with private Pool in Boston's Elite Enclave

An outdoor swimming pool is surrounded by a spacious patio and lush greenery. Sun loungers are arranged around the pool, with a shaded seating area nearby. The house features a multi-level deck overlooking the pool, creating a relaxing outdoor space for guests.

Home in Hopkinton

4.95 out of 5 average rating, 159 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

A clear blue pool reflects the surrounding area, framed by a patio with lounge chairs. A shaded seating area is visible next to the pool, enhancing outdoor relaxation options.

Home in Worcester

4.96 out of 5 average rating, 106 reviews

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

Top guest favorite

The exterior of a two-story house is displayed, featuring white siding and red shutters. A well-maintained front yard is visible, showcasing green grass and shrubs. A brick pathway leads to the front door, framed by two planters with greenery.

Home in Arlington

4.95 out of 5 average rating, 37 reviews

Beautiful Spacious 4BRM House!

Top guest favorite

An inviting bedroom features wood-paneled ceilings and soft lighting. A spacious bed is situated near a window with light filtering through. A vintage-style chair and a wooden bench add to the room's charm, complemented by a decorative area rug underfoot.

Home in Norwood

4.96 out of 5 average rating, 54 reviews

the house of id; vintage shop, accessible space

The backyard features a shared pool surrounded by a brick patio, reflecting the greenery of nearby trees. The area is enclosed by a fence, providing a sense of privacy. A wooden bench is visible nearby, offering a spot to relax by the water.

4.97 out of 5 average rating, 99 reviews

Spacious vacation unit in premium suburban town

A vibrant outdoor pool area features a clear blue pool surrounded by a spacious patio. Lounge chairs are neatly arranged alongside the pool, with manicured shrubs and flowers adding color to the landscape. A privacy fence partially encloses the space, creating a secluded atmosphere.

Home in Waltham

4.91 out of 5 average rating, 56 reviews

Quiet/Private Neighborhood

Weekly house rentals

The exterior of a charming, two-car garage is showcased, featuring natural stone and a shingle roof. Wooden double doors with decorative hardware are visible, along with a basketball hoop attached to the side. The surrounding landscape includes lush green grass and trees.

Home in Westwood

4.82 out of 5 average rating, 91 reviews

sweet little house

The charming exterior of the 1897 home features a wraparound porch adorned with flags and seasonal decorations. A well-maintained yard displays decorative stone borders, mulch, and blooming flowers, framed by lush green trees and shrubs.

Home in Sudbury

4.94 out of 5 average rating, 67 reviews

Historic Victorian Home - Family + Pet Friendly

The image displays a vibrant game area featuring a vintage arcade machine alongside a stylish, modern kitchen. A cozy bedroom with a spacious bed and decorative pillows is seen, as well as a dining space with a round table and upholstered chairs.

Home in Coolidge Corner

5 out of 5 average rating, 4 reviews

Union Haus - Entire Home|2 King Suites|sleeps 10

Top guest favorite

The two-story colonial home features a combination of gray siding and dark shutters. A covered entrance is surrounded by manicured bushes and a small set of front steps, inviting guests into a welcoming space. The yard is well-kept, adding to the neighborhood charm.

Home in Norwood

4.95 out of 5 average rating, 44 reviews

The Cozy Colonial - 4 BDRM house with parking

A spacious living area is presented with soft beige walls and a wooden floor. A light gray sectional sofa and a cozy armchair are arranged around a coffee table. A wall-mounted TV is positioned across from the seating, with art pieces enhancing the ambiance. Natural light floods in through two windows.

Home in Framingham

4.81 out of 5 average rating, 31 reviews

Very nice home close to Boston

Top guest favorite

A serene view of the clear lake is framed by bare trees and gentle foliage, reflecting the blue sky above. The calm water creates a peaceful atmosphere, inviting relaxation and tranquility.

Home in Framingham

5 out of 5 average rating, 57 reviews

Lake Cochituate Waterfront Home

A view of the calm water on Mirror Lake is framed by a flower-lined, stone patio leading to a wooden dock. The water reflects the greenery from the surrounding trees under a clear blue sky.

Home in Wrentham

4.95 out of 5 average rating, 88 reviews

Relaxing Waterfront Lake House

A single-story home is nestled among green trees, featuring a light-colored exterior with red shutters. The driveway leads to the front door, surrounded by well-maintained landscaping and a grassy lawn.

Home in Framingham

4.96 out of 5 average rating, 89 reviews

Quiet Northside Home in Framingham

Private house rentals

A pathway is framed by lush greenery and vibrant flowers, leading to a gazebo nestled among trees. The concrete path is flanked by hydrangeas and other plants, creating a serene outdoor space for guests to enjoy.

Home in Waltham

4.83 out of 5 average rating, 6 reviews

# 216-5 Private bath & entry

A spacious living room features a large flat-screen TV mounted on the wall, complemented by decorative plants on a console. Neutral-colored walls are adorned with two abstract art pieces. A round, golden coffee table sits in the center, surrounded by a comfortable sectional sofa.

4.83 out of 5 average rating, 29 reviews

Chic and Cozy Family Retreat Close to Boston

A neighborhood scene displays a charming yellow house with white trim and a welcoming front porch. A rainbow arcs across the sky, casting colorful reflections over the green grass and sidewalks. A small child can be seen walking on the path, lending a sense of community to the tranquil setting.

Home in West Roxbury

4.9 out of 5 average rating, 10 reviews

Charming Boston Single Fam Home Near Commuter Rail

The exterior of a Victorian-era home is surrounded by lush greenery, with vibrant flowers lining the pathway. A spacious porch is visible, framed by tall trees, inviting guests to enjoy the natural setting. A gravel driveway leads to the welcoming entrance.

Home in Waltham

4.93 out of 5 average rating, 99 reviews

Harvard House-The Gathering Place.

Top guest favorite

The living area features a spacious leather sectional sofa, complemented by vibrant cushions and a textured green throw. A modern television is mounted on the wall, surrounded by large windows that provide ample natural light. A lush plant adds a touch of greenery to the space.

Home in Waltham

4.98 out of 5 average rating, 49 reviews

Large House KingBed European Look near MoodySt 4BR

The dining area features a round glass table surrounded by five upholstered chairs, positioned beneath a decorative light fixture. A spacious kitchen bar with four stools is visible in the background, complemented by large windows allowing natural light to fill the space.

Home in Roslindale

4.99 out of 5 average rating, 79 reviews

Upscale Boston 2 BR w/ Off Street Parking

A bright living room features two brown sofas and a coffee table at the center. Natural light filters through large windows adorned with sheer white curtains. A television is mounted on the wall, and a side table with decorative items adds a homely touch.

Home in Norfolk

5 out of 5 average rating, 5 reviews

Cleveland St. Oasis

Top guest favorite

A backyard space features four Adirondack chairs arranged around a fire pit, with gentle string lights strung overhead. A green lawn provides a soft surface, while trees and plants enhance the natural setting, creating an inviting atmosphere for outdoor gatherings.

Home in Brockton

5 out of 5 average rating, 42 reviews

Large Private Home with Patio firepit and Grill

Quick stats about house rentals in Wellesley

Total rentals
40 properties
Total number of reviews
1.8K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Destinations to explore