Holiday houses in Weston

4.98 out of 5 average rating, 145 reviews

A comfortable seating area is highlighted by two stylish armchairs and a soft sofa. Natural light filters through large windows that overlook the greenery outside. A modern rug is placed on the wooden floor, complementing the decor, while a lamp and coat rack add functional touches.

Home in Framingham

Cozy en suite w/ high ceilings

Relax in this peaceful private en-suite with breathtaking backyard views of the tall pine forest. Natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. Just 25 min to Boston, 40 min. to Gillette Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Very safe walkable neighborhood

5.0 out of 5 average rating, 211 reviews

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

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.

4.89 out of 5 average rating, 56 reviews

A cozy living area features a dark sectional sofa and a light wood coffee table positioned on a textured area rug. A television is mounted on the wall across from the seating, complemented by a small lamp on a side table. Natural light filters through multiple small windows.

Apartment in Wayland

Cozy lakeside retreat

Take it easy at this unique and tranquil getaway a perfect spot to recharge and enjoy all Dudley Pond has to offer.Relax on the deck overlooking the water OR explore on a canoe, kayak, or paddleboard OR walk to TheChat (an old speakeasy) for yummy drinks and food. Centrally located in the Metrowest suburbs close to the Mass turnpike and public transportation to downtown Boston. Close to Babson, Wellesley College, Boston University, Brandeis, Framingham State for graduation or parent weekends.

Superhost

A spacious living area features two gray sofas with yellow accent pillows, arranged around a circular wooden coffee table. A gas fireplace is centered against a white mantel, complemented by large windows allowing natural light and views of greenery.

Townhouse in Waltham

Boston's Luxury Home: Pet-Friendly, 4BR, Sleeps 10

Luxury, modern, bright townhouse offering a gourmet kitchen is available for your next getaway. Just 1 min walk to Waltham Rail Station (some ambient rail sounds possible), buses to downtown, famous Moody street & Main street with 50+ restaurants, grocery, ALL WITHIN WALKING DISTANCE. Easy commute to anywhere within Waltham, Boston, Cambridge, Watertown. Ideal place for working professionals, families, or someone visiting Boston for the weekend. ATTACHED GARAGE PARKING INCLUDED for 2 cars.

4.93 out of 5 average rating, 162 reviews

4.86 out of 5 average rating, 43 reviews

New Top Floor Spotless Waltham Condo Walk To Shops

Welcome to Waltham! Stay in this beautifully remodeled 3-bed condo tucked away on a quiet side street, yet just one block from vibrant Moody Street. Walk to top restaurants, pubs, coffee shops, and local shopping Commuting? The MBTA bus and commuter rail are nearby with direct service to Boston’s North Station. 3 comfortable bedrooms 1 full bath Dedicated laundry in the building Private driveway parking for 2 car + free street parking A stylish, relaxing home for your next Boston-area trip

4.94 out of 5 average rating, 397 reviews

A spacious living room is seen with polished hardwood floors. There is a flat-screen TV on a dark cabinet, and a coffee table featuring a small potted orchid. Archways frame the entry to the kitchen, visible through the open door, highlighting the room's welcoming design.

Apartment in Waltham

Spacious & Clean 2 BR- 15 mins to Boston

My place is close to vibrant Moody Street full of restaurants, ice cream shop, Dunkin Donuts, grocery store, shops and a movie theater. 15 minutes to Boston, and close to Brandeis University, Regis College, Bentley College, Laselle College, Boston College, Charles River and more. You’ll love my place because of the comfy bed, cleanliness, the ambiance, the light, and the neighborhood. My place is good for couples, solo adventurers, business travelers, families (with kids), and big groups.

Superhost

A spacious bedroom features two neatly made beds, one larger and one smaller, adorned with white bedding. A bedside table holds a lamp, and a window with light curtains allows natural light to enter, complemented by warm LED ceiling lights.

4.84 out of 5 average rating, 153 reviews

Lovely one bedroom apartment condo, with parking

The whole group will enjoy easy access to everything from this centrally located place. Entire unit. In the heart of Waltham Large and comfortable one bedroom apartment in quite condominium style place. Great location 5 minutes walk to train or bus to Boston, 6 minutes walk to Moody street where all the restaurants and attractions are currently open. Also 7 minutes drive from Brandeis university or Bentley College . We are located near everything you would need to do in Waltham. The

4.93 out of 5 average rating, 15 reviews

Apartment in Weston

Bright Private Quiet Apartment – 30 min to Boston

This is a self-contained basement guest apartment in our home, with its own private entrance, bedroom, huge living room, bathroom with shower, smart toilet with bidet, and kitchenette. Forget your worries in this spacious and serene space. Best for 2–3 people visiting, attending local events, or exploring Boston while staying in a quiet suburb. Free parking for upto three vehicles. Easy access to I-95 (128), I-90, Route 9, amazing restaurants, and 12 miles away from Boston city.

4.92 out of 5 average rating, 12 reviews

Home in Framingham

Retreat Near Boston | AC, BBQ, Deck, Pets OK

Welcome to your perfect home base just outside Boston—ideal for families, groups, and business travelers alike. This bright and spacious 4-bedroom home comfortably accommodates your group with 5 beds and plenty of room to relax. Enjoy a fully fenced in backyard. Enjoy a large, sun-filled living area, a bonus dining space with beautiful vaulted ceilings, Kawaii Piano, and a fully equipped kitchen with modern stainless steel appliances—perfect for gathering and entertaining.

4.89 out of 5 average rating, 133 reviews

Home in Wayland

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.

4.97 out of 5 average rating, 189 reviews

A private entrance to the basement suite is framed by a modern railing and steps leading down. Lush greenery surrounding the entrance enhances the serene setting, while a light fixture is positioned above the door. A children's playset can be seen in the background.

Guest suite in Lexington

Modern Farmhouse Suite in Historic Lexington

Enjoy a modern farmhouse themed private suite in a peaceful setting in historic Lexington. Our home is perfect for : -Travelers visiting Boston and surrounding historical sites -Visitors seeking to stay in close proximity to family and friends in Lexington or surrounding communities -Locals in need of temporary housing -Business professionals needing accommodations within commuting distance to Boston -Families with kids, couples, or solo guests

4.89 out of 5 average rating, 61 reviews

Bright, sunny 1 bedroom condo

Bright, spacious 1 bedroom condo in Waltham center. Spacious bedroom with a queen size bed. Living room with a large screen TV, leather furniture and separate work area. Additional twin size beds can be set up on request for a total of up to 4 guests. Minutes to a busy Moody St nightlife. Steps to Waltham center train stop that will take you to downtown Boston in about 20 minutes. Parking spot for 1 car.

Popular amenities for Weston holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Weston

4.8 out of 5 average rating, 371 reviews

A well-lit bedroom features a spacious bed adorned with patterned bedding. Natural light filters through two large windows with wooden blinds, illuminating the soft carpeted floor. A bedside lamp provides additional warmth, and a door is partially visible on the right.

Guest suite in Wellesley

Private suite 1 BR, 1 BA, 1 LR, 1 FLR

Apartment in Waltham

Super Modern 2 Bed in Waltham

5.0 out of 5 average rating, 3 reviews

Apartment in Weston

18 Mi to Boston - Stylish Unit in Upscale Enclave!

4.83 out of 5 average rating, 6 reviews

The living area features hardwood flooring with a warm tone. A comfortable brown leather sofa is positioned opposite a small black ottoman. A wooden cabinet and a side table are visible, while light from large windows brightens the space. Soft-colored artwork decorates the walls.

4.69 out of 5 average rating, 164 reviews

Modern 2 Bedroom with Parking

4.98 out of 5 average rating, 47 reviews

An inviting living area features a red, blue, and cream area rug centered on a wood floor. A day bed with patterned cushions is positioned against a brick wall, while natural light enters through a large window overlooking greenery. A small desk and a second seating area are also visible.

Guesthouse in Waltham

Private In-Law

Guesthouse in Sudbury

Carriage House

5.0 out of 5 average rating, 4 reviews