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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

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

4.97 out of 5 average rating, 105 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.

A charming multi-family house is featured, showcasing a well-maintained exterior. The light-colored siding is complemented by dark shutters. A white picket fence borders the property, and the driveway provides access to the main entrance, flanked by a small garden area.

Home in Hyde Park

4.85 out of 5 average rating, 315 reviews

~*Pet Friendly 30min to Downtown*~ THE BOSTONIAN

Relax in the Bostonian, a stylish, pet-friendly apartment on the semi-basement level of a charming multi-family house. The apartment is air conditioned & overlooks a beautiful patio and backyard. Located in quiet Hyde Park neighborhood, a 30 minute drive into downtown Boston. Plenty of free streetside parking. Private in unit laundry. Professionally cleaned. Room 1: Queen size bed Room 2: Queen size bed Room 3: Living room couch, TV, electric fireplace Dining room: includes two wall arcades

The exterior of a two-story brick house is shown, featuring a gray roof and multiple windows. A neat front yard is enclosed by a chain-link fence, with a nearby stop sign visible. The entrance is marked by a set of steps leading to a central door.

Home in Newtonville

4.95 out of 5 average rating, 140 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, 343 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.

A cozy living area is presented, featuring a modern black sofa and two soft pink ottomans. Natural light streams in through the window, illuminating the space. Decorative shelves with plants and artwork add a touch of greenery and charm to the room.

Home in Stoneham

4.92 out of 5 average rating, 280 reviews

Entire Apartment in Stoneham

Welcome to our cozy, beautiful, and well-equipped home—your perfect retreat in the heart of Stoneham. Wake up in this bright and inviting apartment, just 20 minutes from the airport and the historic city of Boston. You’ll be conveniently close to shopping malls, restaurants, coffee shops, grocery stores, and the stunning nature of Middlesex Fells Reservation and Stone Zoo. Whether you’re here to explore or unwind, this charming home will make your trip both enjoyable and stress-free.

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

4.93 out of 5 average rating, 160 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

A modern kitchen area is presented with wooden cabinetry and black appliances, including a refrigerator and microwave. A dining table with place settings is visible, alongside a cozy living area featuring a leather sofa and a ceiling fan overhead.

Home in Framingham

4.96 out of 5 average rating, 140 reviews

1BR Loft | 25 Mins to Boston | Quiet Neighborhood

Welcome to The Loft! 100% Private 1-Bedroom Place Queen Bed — Pillowtop Mattress Full Kitchen — Stove, Fridge, Dishwasher, Pots/Pans, Utensils & Cooking Essentials Dining Area — Table & Chairs Living Room — Leather Sofa 49" SmartTV — Netflix + Sling Live TV Bathroom — Shower, Plush Towels & Natural Bath Products Private 2nd Floor Entrance Your Own Driveway Quiet & Safe Neighborhood Deep Cleaned & Sanitized 2 Min Walk to Park 25 Mins to Boston Easy Access —Route 9 & 90-Mass Pike

A welcoming entrance is depicted, featuring a bright blue door framed by shrubs and flowers. A row of mailboxes can be seen beside the path, complemented by a wrought iron railing and planters that add greenery to the scene.

4.97 out of 5 average rating, 150 reviews

Artist's Haven (2)

Explore Quincy/Boston from my spotless home! As a Superhost, I'm committed to providing a memorable stay to earn your 5-star review. Experience a vibrant, artsy, and tranquil environment that mirrors my passion for art. This immaculate, peaceful 1-bedroom apartment on the SECOND floor is crafted for a perfect energy flow—a sanctuary of creativity, designed, and adorned with my original artworks, adding a unique and inspiring touch to every corner. Certificate # STR-23-8

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, 100 reviews

Harvard House-The Gathering Place.

HARVARD HOUSE - The Gathering Place--- Beautiful Home, Magical Property A magical atmosphere ideal for small weddings, birthdays, graduations, celebrations of life. team building "Harvard House is an amazing place, it helped our family renew the ties that bind." "The team created a shared vision, conflicts got ironed out, we built a rallying momentum." "Our wedding at Harvard House was amazing." "Our group split the costs which made it affordable."

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 Village

4.92 out of 5 average rating, 142 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!

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, 261 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.

Home in West Newton

4.91 out of 5 average rating, 165 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.

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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, 170 reviews

Nana-tucket Inn

Top guest favorite

5 out of 5 average rating, 27 reviews

Elegant Spacious Retreat with Prime Boston Access!

Top guest favorite

Home in Hopkinton

4.95 out of 5 average rating, 161 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

Top guest favorite

Home in Greendale

4.96 out of 5 average rating, 110 reviews

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

Top guest favorite

A well-maintained swimming pool is featured in the backyard, surrounded by a patio. Lush greenery and mature trees offer privacy. The two-story house is visible in the background, with large windows allowing light to enter. A basketball hoop is positioned adjacent to the pool area.

Home in Arlington

4.95 out of 5 average rating, 41 reviews

Beautiful Spacious 4BRM House!

Top guest favorite

A vibrant living area is highlighted by a plush brown sofa and an elegant coffee table. A whimsical rug with colorful patterns adds warmth to the space. A vintage record player is displayed on a decorative stand, while artistic wall decor and soft seating create an inviting atmosphere.

Home in Norwood

4.97 out of 5 average rating, 59 reviews

the house of id; vintage shop, accessible space

Top guest favorite

The exterior of the duplex unit features a charming yellow siding and a brick chimney. A front deck with white railings offers access to the main entrance, while landscaped greenery surrounds the area, enhancing the welcoming ambiance.

4.97 out of 5 average rating, 104 reviews

Spacious vacation unit in premium suburban town

A welcoming entrance is displayed with a polished brick pathway leading to a well-maintained white house. The front features large black-framed windows and a pair of bold red doors flanked by pots of colorful flowers, complemented by lush green landscaping.

4.86 out of 5 average rating, 35 reviews

Hidden Gem near Boston w/ Private lake access

Weekly house rentals

Top guest favorite

Home in Roslindale

5 out of 5 average rating, 20 reviews

New modern 2bd condo: free parking/near train

Home in West Roxbury

4.94 out of 5 average rating, 17 reviews

Charming Boston Single Fam Home Near Commuter Rail

A spacious patio is equipped with a round dining table and eight wicker chairs beneath a large blue umbrella. In the background, a grassy area features a wooden playset with slides and swings, surrounded by lush trees.

Home in Cochituate

4.91 out of 5 average rating, 100 reviews

Spacious 4 bedroom home with large yard

Home in Sudbury

4.95 out of 5 average rating, 75 reviews

Historic Victorian Home - Family + Pet Friendly

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

4.96 out of 5 average rating, 45 reviews

The Cozy Colonial - 4 BDRM house with parking

Home in Waltham

4.73 out of 5 average rating, 26 reviews

# 216-B lower level entire studio w/ private bath

Sturdy wooden stairs lead to the upper floor, highlighted by a decorative railing. A framed cityscape artwork hangs on a yellow wall, adding visual interest. Light pours in from an overhead skylight, illuminating the staircase and adjacent landing area.

4.98 out of 5 average rating, 46 reviews

Victorian fully renovated! T station-Boston 20'!

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 Cochituate

5 out of 5 average rating, 62 reviews

Lake Cochituate Waterfront Home

Private house rentals

The modern two-story home features a blue exterior with white trim and three windows on the ground level, complemented by decorative planters. A bold red front door is centrally positioned, enhancing the welcoming entrance.

Home in Charlestown

4.96 out of 5 average rating, 68 reviews

Spacious & Pet-Friendly Modern Home in Charlestown

Top guest favorite

5 out of 5 average rating, 20 reviews

Cozy by the coast! Long Term deals!

Top guest favorite

The exterior of the home is presented, featuring a light blue facade with white trim. A spacious deck is visible on the upper level, while a neatly landscaped yard with a manicured lawn and stone walkway leading to a white picket fence invites a welcoming atmosphere.

Home in Marblehead

5 out of 5 average rating, 27 reviews

Marblehead Neck Cottage, Harbor Views & Roof Deck

A stylish living room is showcased, featuring a comfortable brown sofa, a glass coffee table, and a decorative area rug. Large windows allow natural light to fill the space, complemented by soft lighting and elegant curtains. A modern fireplace adds warmth to the inviting atmosphere.

Home in Jamaica Plain

5 out of 5 average rating, 4 reviews

Boston Buccaneer Retreat

Top guest favorite

Home in Cambridgeport

4.99 out of 5 average rating, 70 reviews

Pvt Bedrm/Bathrm/Kitch'ette on Quiet Tree Lined St

The exterior of a multi-story residential building is shown, featuring a warm red and cream color scheme. Large windows, adorned with flower baskets, offer a welcoming appearance. Surrounding greenery enhances the setting, while a fenced yard and parking area are visible.

Home in Roslindale

4.89 out of 5 average rating, 62 reviews

Kailyn Apartment Boston, Massachusetts

Top guest favorite

A front porch features white railing and a cozy seating area with patterned cushions. The view includes a spacious green lawn and a bright, open sky with clouds, creating a tranquil outdoor setting.

Home in Brockton

5 out of 5 average rating, 48 reviews

Peaceful Oasis: King Bed, Fire Pit, & Grill

A dining area with a round wooden table surrounded by four dark chairs is seen. Against a white wall, a full-size fridge and a sleek kitchen with white cabinetry and utensils are visible. A piece of framed art adorns the wall, adding a modern touch.

Home in Arlington

4.81 out of 5 average rating, 21 reviews

Cozy studio in calm neighborhood

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