Holiday houses in Boston

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Top-rated holiday rentals in Boston

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

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Top Guest favourite
A charming two-story cottage is nestled within lush greenery, showcasing a well-maintained exterior with a sloped roof and welcoming front porch. Vibrant flowers and shrubs surround the entrance, enhancing the peaceful outdoor ambiance. A clear blue sky complements the serene landscape.
Cottage in Bethel Park
5 out of 5 average rating, 116 reviews

"The Cottage on Summit"

The "Cottage on Summit" is charming & updated Historical 1932 Cape Cod, located in the beautiful Bethel Park community. Relax with the whole family in our peaceful, cozy yet spacious home, boasting privacy, comfort and safety, nestled within the Summit neighborhood . SPECIAL NOTE: A "request to book" will need additional information prior to "confirming by the host" Verified ID and at least TWO 5 star previous reviews are required. Please read house rules which must be "strictly followed".

Guest favourite
The exterior of Highland House is depicted, featuring a wooden deck with potted flowers and outdoor seating. Large windows allow natural light to fill the space, and solar panels are visible on the roof. The landscape in the background offers a view of open fields.
Tiny home in Mount Pleasant
4.97 out of 5 average rating, 325 reviews

Tiny House - Big Farm Adventure near Pittsburgh

Enjoy an Adventure in "Glamping" at Highland House on Pittsburgher Highland Farm. This custom built Tiny House is situated on over 100 acres of rolling farmland, hills and forests, with Scottish Highland cattle, chickens, sheep & lambs, pigs, fish in the pond, and 2 beehives. You have use of the entire farm during your stay. Located about 45 minutes south-east of Pittsburgh in Pennsylvania's beautiful Laurel Highlands, there is lots to see and do both on site and nearby. Photos current 2024.

Superhost
The exterior of the house is shown, featuring a well-maintained brick facade. The covered porch leads to the front door, framed by two windows. Lush grass surrounds the walkway, emphasizing the welcoming entry. A hint of greenery is visible in the background.
Home in Monroeville
4.82 out of 5 average rating, 230 reviews

Pittsburgh Hideaway - Pets - Private

-Discounts on weekly and monthly stays - Put in dates for prices. -1 bedroom house with 1 bath and everything you need for a comfortable stay. -House is tucked away, but also close to the highway and turnpike. -Walking distance to UPMC East, 6 minutes to Forbes Hospital, and min from major shopping/restaurants. -Pet friendly with a large yard (no fence). -Dog park only 7 minutes away - Monroeville Dog Park. Boyce Park and Penn Hills (fenced dog parks) 15 min away -TV- Amazon Stick to login

Top Guest favourite
A retro-inspired kitchen is equipped with mint green appliances and sleek white cabinetry. Countertops are complemented by a backsplash of white tiles, while natural light enters through a window with horizontal blinds. A dining table is positioned nearby, enhancing the kitchen's functionality.
Bungalow in Carnegie
4.97 out of 5 average rating, 207 reviews

Groovy Retro Get-Away

With a retro flare & a mid-century modern vibe, you'll enjoy this quaint bungalow in a quiet residential neighborhood conveniently located minutes from downtown Pittsburgh, the airport, many great sites, must-see attractions, universities & colleges. Whether you're in town for business, a sports event, bringing a student back to school or just want some time away, this cozy space is perfect! Everything in this bungalow is well appointed including keurig coffee, WiFi & a smart TV for streaming.

Top Guest favourite
A light-filled living area displays a comfortable sofa paired with an accent chair and a round coffee table. A dining area with bar stools is visible, along with a modern kitchen featuring stainless steel appliances and stylish cabinetry. Warm wooden flooring adds to the inviting ambiance.
Apartment in Shadyside
4.91 out of 5 average rating, 171 reviews

Cozy King Suite with Parking!

In the heart of Shadyside! 1 Block to Walnut St w/ FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 1BR/1 bath apartment in a prime location, with all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted & entirely remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances & in-unit laundry is brand new!

Guest favourite
A cozy living area is highlighted by a sleek beige leather sofa, accompanied by decorative pillows. A glass coffee table sits on an ornate area rug, while natural light illuminates the space. The staircase and a softly lit hallway can be seen in the background.
Home in Duquesne
4.91 out of 5 average rating, 252 reviews

Entire home near Kennywood without extra fees.

Bring everyone along for the trip, including Fido! Our home is a cozy, yet spacious Cape Cod southeast of downtown Pittsburgh. The backyard faces a beautiful and peaceful meadow. The yard is fenced in and has a small garden filled with herbs and tomatoes during the summer. Our home has all of the amenities to make your stay enjoyable and easy. We keep our home clean, organized and stocked with essentials. The beds, pillows and sheets are new and comfortable. Parking is plentiful and easy!

Guest favourite
A welcoming entryway features a small dining table beside a black couch adorned with cushions. Wall-mounted shelves showcase dishware and decorative items. Framed photographs hang on the wall, and a door with a window allows natural light to brighten the space.
Guest suite in West Mifflin
4.95 out of 5 average rating, 211 reviews

Hilltop Suite, Quiet Street

Your suite has your own entrance through the back of the house as well as onsite parking in the driveway. You are in your own PRIVATE area that does not join with my living area in any way. Inside, I’ve worked hard to make the space very updated and clean. Amenities include your own bathroom with a deluxe shower, an in-suite mini kitchen with stove and fridge, a small dining table, a couch, and a comfy queen bed. It is approximately 15 mins to all main universities and the city center.

Top Guest favourite
An open interior space showcases rich wooden walls and a vaulted ceiling with warm lighting. A dining table, set for meals, is positioned near a window. The kitchen area is visible, equipped with modern appliances, and the entrance features a rustic wooden door.
Cottage in Mount Pleasant
5 out of 5 average rating, 234 reviews

Sunbeams Cottage

Small home is completely remodeled using traditional woodwork craftsmanship for a warm feel. Full appliances and amenities are supplied in the cottage. Evening and breakfast snacks included. Tasty public tap water for drinking and cooking. Private lane leads to the home with a spacious covered porch overlooking hillside and field. Ideal location at foothills of Laurel Highlands and outskirts of Pittsburgh. Town of Mt. Pleasant is just minutes away providing restaurants and shopping.

Guest favourite
A spacious living area features a comfortable blue sofa positioned against a light gray wall, adorned with decorative mirrors and wall art. A large area rug lies on the polished wooden floor, complementing the white fireplace and a flat-screen television mounted above it.
Home in East McKeesport
4.93 out of 5 average rating, 150 reviews

McClure Manor - 3 King Bedrooms

Step into the warmth of McClure Manor! Just 14 miles from the heart of downtown Pittsburgh and nestled near the trendiest neighborhoods, this inviting haven offers not only proximity to Route 30 and the turnpike but also unparalleled convenience to explore all that Pittsburgh has to offer. Make this your ideal home base, effortlessly connecting you to the vibrant pulse of the city. *If you enjoy this home, the owners are amenable to selling! Please contact us for more information

Superhost
A covered porch features comfortable seating on a patterned rug, accompanied by a glass-top table. Lush greenery is visible beyond the railing, creating a relaxed outdoor space for lounging.
Home in Elizabeth
4.87 out of 5 average rating, 109 reviews

Our Guest Home

*****THIS HOME IS NOT SHARED***** Relax with the whole family at this peaceful country home, located 20 minutes from Pittsburgh, central to various parks, eateries, shopping areas & 3 casinos (each 19 miles away) 1.5 miles off route 51. Located on a private lane with plenty of room to park, trucks, campers & atvs welcome. The home also has an animal/dog outside enclosure so your furry friends can play outside! (This is a shared dog yard from time to time with our golden doodles)

Guest favourite
An inviting private hot tub is situated in a fenced backyard area, surrounded by soft lighting and decorative plants. The brick wall of the house provides a rustic backdrop, creating a cozy ambiance at dusk.
Townhouse in Central Lawrenceville
4.91 out of 5 average rating, 319 reviews

Hot Tub, King Bed, Cabin Vibes in Lawrenceville!

With cozy cabin vibes, exposed brick, and designer touches, this romantic getaway is perfect for couples or a relaxing stay. Escape to a rustic-modern retreat in the heart of Lawrenceville, just one block from Butler Street! Unwind in the private hot tub, snuggle up on the couch by the fireplace, or explore the city's best dining and nightlife just steps away. Completely remodeled in January 2025 with luxe amenities—book now for an unforgettable stay!

Top Guest favourite
The living room features a comfortable gray sofa and matching armchair, complemented by a wooden coffee table centered on a decorative area rug. Natural light filters through large windows, and table lamps provide additional illumination. Two decorative cushions add a subtle touch to the seating.
Home in Irwin
4.98 out of 5 average rating, 178 reviews

Our cozy contemporary home near PA turnpike

Enjoy this peaceful, private residence conveniently located <5 miles from PA turnpike exit 67 with quick access to many restaurants and retail establishments. This is a nicely appointed and recently renovated ranch home in a residential neighborhood with a peaceful outdoor space. There is an open concept living room, dining area and new modern kitchen with stainless steel appliances. The bedrooms have comfortable beds with down comforters .

Popular amenities for Boston holiday rentals

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  2. United States
  3. Pennsylvania
  4. Allegheny County
  5. Boston