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, 111 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.

Guest favorite
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.
Home in Dedham
4.93 out of 5 average rating, 118 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, 253 reviews

2BR Lovely 1900s Home | 25 Min to Boston | 1200ft²

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

Guest favorite
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, 351 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
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, 305 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.

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
4.93 out of 5 average rating, 168 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

Top guest favorite
A spacious bedroom is illuminated by natural light from large windows, featuring a comfortable bed with soft linens. Two plush armchairs are positioned across from a cozy sofa. A modern glass coffee table holds a magazine, while decorative elements add charm to the setting.
Home in Cambridge
4.94 out of 5 average rating, 306 reviews

Stunning urban hideaway nearby Harvard Square

Charming apartment in a 19th century Victorian house conserves its period architectural details in recently renovated comfort. Light streams into this en-suite guest residence through gracious windows. Beautiful cabinetry and bookcases offer some evening reading. Enjoy the marble bathroom and hardware floors and well-appointed kitchenette. A stone's throw from Porter Square, where bars, cafes, boutiques, and transportation options abound. Minutes to Harvard, MIT and Boston.

Top guest favorite
The kitchen area features a modern design with a sleek, round dining table surrounded by four transparent chairs. Stainless steel appliances, including a refrigerator and stove, are present, complemented by wooden cabinetry. Natural light enters through a window, illuminating the polished hardwood floor.
Home in Brighton
4.86 out of 5 average rating, 222 reviews

Comfortable house w garden and parking, close to T

The house is conveniently located 15-20 mins from downtown and 25 mins from the airport by taxi. There is a train and bus stations close by and there are lots of restaurants and stores (whole foods has everything) in a walking distance. There is a driveway parking that fits 3 cars. The house offers 7 sleeping places which is perfect for families and groups however there is no living room. Great place to stay with dogs as there is a backyard and lots of walking options.

Guest favorite
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
4.95 out of 5 average rating, 101 reviews

Quiet Northside Home in Framingham

This quiet three bedroom home with 1.5 baths has a full kitchen. You can enjoy breakfast in the kitchen nook and more substantial meals in the dining room. Two separate living spaces—a living room and a large family room with Smart TV and office area—allow group members to pursue different activities. The main bedroom has an attached half bath for privacy. The quiet residential neighborhood has two parks and hiking trails just a few blocks away.

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.
Home in Dedham
4.98 out of 5 average rating, 272 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.

Guest favorite
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, 175 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.

Guest favorite
A spacious deck features a rectangular dining table surrounded by six black metal chairs. Lush greenery and the serene lake are visible in the background, with a clear sky and scattered clouds above, creating an inviting outdoor space.
Home in Hudson
4.9 out of 5 average rating, 103 reviews

Lake home

Enjoy the lake view from the dining room, living room and bedroom! There is a deck with a BBQ, full kitchen, 1 bedroom and 1 bathroom. For 2 guests only please. No parties or gatherings allowed. The beach / dock will be shared the the tenant below. Use of kayaks, paddleboard and canoe is allowed.

Popular amenities for Wellesley house rentals

When is the best time to visit Wellesley?

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Quick stats about house rentals in Wellesley

  • Total vacation rentals

    Explore 40 vacation rentals in Wellesley

  • Nightly prices starting at

    Wellesley vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 1,880 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Wellesley vacation 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!