
House holiday rentals in Winthrop
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Top-rated house rentals in Winthrop
Guests agree: these houses are highly rated for location, cleanliness and more.

Ocean Views at Casa de Mar near Salem & Boston
Relax and unwind at Casa de Mar - our 3 bed, 3 full bath seaside home on the North Shore. Close to Salem and Boston, overlooking Swampscott Bay to Nahant. The great room has 25' ceilings, a 70" flat screen TV, a desk, and 2 seating areas. Modern kitchen, new appliances. The master bedroom has a king-sized bed, sitting area, flat screen TV, private balcony, and en suite bath. The first floor bedroom has a queen bed and a private balcony. The third bedroom has a queen bed and en suite bath.

Renovated Cozy City Getaway
Newly renovated cozy 1 bedroom home located on the hills of Beachmont, walking distance from the MBTA train station and Revere Beach. Enjoy sitting on the deck overlooking the Belle Isle Marsh Reservation and Boston Logan Airport in the distance. Take a walk along the beach or take the train into Boston. The location is a 5-10 minute ride to the Airport and a 15 minute train ride to downtown Boston. The unit has new furnishings (2021), modern appliances, and is beautifully decorated.

Cozy & Modern 2 Bedroom House - Free Parking !
Welcome to our charming, renovated bungalow near Tufts University has been meticulously cared by owner and is ready to welcome new guests. Enjoy 2 beds/1 bath, private parking, and walkable access to Medford's attractions including; banks, shopping centers, local restaurants/cafes, Encore casino, public transportation, Middlesex Fells Reservation and much more. Tastefully furnished with new queen beds, remote work setup, a relaxing living area, and a fully equipped kitchen for your comfort.

Authentic Rustic Single Family Home in Old Town
Restored 1800's little single family home. Cozy, clean and artistically renovated to retain authenticity. Located in Old Town - walk to everything! Back yard patio with BBQ, perfect for morning coffee. Off street Parking! 4.6 miles to salem witch museum. Boston is 19 miles. Starbucks is a 2 minute WALK. Explore our little town and fall in love. Please this is not a party house. It is in a tiny little neighborhood. Quiet time 10pm - 8am. I want my precious home back in clean condition. Thx

~*30min to Downtown*~ THE COSMOPOLITAN
Stylish contemporary kid-friendly apartment on the first floor of a multi-family. Bright and roomy bedrooms with a large eat-in kitchen. Central air conditioning. Plenty of free street parking. Access to shared laundry room. Located in Hyde Park neighborhood, 30 minute drive into downtown Boston. Professionally cleaned and disinfected. Room 1: Queen size bed, closet, TV Room 2: Queen size bed, closet Room 3: Living room couch bed, closet, TV Entryway: Includes Mrs. Pac Man wall arcade

Entire Apartment in Stoneham
Welcome to our cozy, beautiful, and well-equipped homeâyour 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. Youâll be conveniently close to shopping malls, restaurants, coffee shops, grocery stores, and the stunning nature of Middlesex Fells Reservation and Stone Zoo. Whether youâre here to explore or unwind, this charming home will make your trip both enjoyable and stress-free.

3 BR Private Family Home, S. Boston/Seaport/BCEC
A beautiful single home all to yourself with a private entrance AND GARAGE PARKING in bustling South Boston! Equipped with 3 private bedrooms as well as two bathrooms and outdoor deck space that opens to a small park, this home features plenty of amenities in an unbeatable location with access to a plethora of shops and restaurants. One mile exactly to the Convention Center (BCEC).This is the perfect place for large groups and companies who seek a quiet comfortable Boston experience.

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.

Sensory Serenity: Parking/Netflix/Wi-Fi/Frag-Free
Stay in our elegant Boho-Modern Home Only 15min from Boston's Major Attractions. âQueen Beds+Organic bedding, cleaned w/ natural cleaners for your BEST rest w/o combatting toxins/fragrances âIdeal for Families and Staycations âInviting Dinning and Large Kitchen âFast WIFI+Netflix âOff-Street Parking âSelf check-ins with secure keypad âLaundry Everything you need is provided - Just pack up your clothes and enjoy your stay with us! Book today to reserve our luxury home!

Prime location near Boston
Home in Everett, MA. Located just a 20 minute walk from Encore Boston Harbor Casino. This location is also just a 15 minute drive from downtown Boston. Room in the basement has a microwave, refrigerator, coffee maker, and hot water for making tea which is provided along with light snacks and coffee. There is a desk for laptop. Queen Tempurpedic Mattress topper as well as a pull out sofa. Private bathroom with spacious shower. See guide book for more info on the area!

10 minutes to Airport-Boston-Casino (2G)
(2G)=Your place is on the 2nd floor and your color code is Green. Do Not include it to the address when you navigate to us. We have a beautiful victorian house built in 1858, owned by our family in 1911, big spaces and high ceilings are a blessing! You can stay here with your family and kids, we have a play room with some toys for fun, a living room, a bedroom and a private full bathroom with a pressure shower. Chelsea is a nice quiet place with a lot to offer.

Clean, spacious In-Law Suite -Near Everything
Immaculately furnished, clean and spacious In-Law Suite features: 1 bedroom, 1 full bath, dining kitchen, and living room located steps from Lynn Woods Reservation (over 30 miles of picturesque New England trails perfect for hiking, running, mountain biking and cross-country skiing) and short drives from beaches, Boston and North Shore. Kids toys, a baby crib and access to a large beautiful upstairs deck and bbq are available upon request.
Popular amenities for house rentals in Winthrop
House rentals with a pool

Luxury Ultra Modern House in Newton ; Boston

NEW! Walk To Beach! Sunshine House

Bauhaus Retreat in Nature Preserve

Boston 15 min away.

Beautiful Spacious 4BRM House!

the house of id; vintage shop, accessible space

Spacious vacation unit in premium suburban town

Large & beautiful home, shared pool and yard
Weekly house rentals

All the comforts of home, quiet city neighborhood

Sunny 3 bedroom on beach

Sea Forever - Oceanfront Home in Nahant!

Cozy & Modern Entire Residential Home â¤ď¸

Newly remodeled home with ocean views!

Luxurious House-Harvard/PorterT 4BR/4Bath, Parking

3 bdr, steps from the ocean, minutes from Boston

Convenient 2BR Condo W/Private Parking in Newton
Private house rentals

Spacious & Pet-Friendly Modern Home in Charlestown

4BR Historic Home|Minutes 2 Downtown Salem|Parking

1850s Charlestown Cottage

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

Entire House Near Boston-Salem - Walk to the beach

Huge NEW Home Boston Harvard MIT Covered Parking

Revere Beach House, Logan Airport, Bay Views

Oceanfront Oasis w/ Expansive Views & 2 Decks
When is the best time to visit Winthrop?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ÂŁ64 | ÂŁ73 | ÂŁ75 | ÂŁ91 | ÂŁ97 | ÂŁ104 | ÂŁ100 | ÂŁ101 | ÂŁ82 | ÂŁ83 | ÂŁ77 | ÂŁ80 |
| Avg. temp | -1°C | 0°C | 4°C | 9°C | 15°C | 20°C | 23°C | 23°C | 19°C | 13°C | 7°C | 2°C |
Quick stats about house rentals in Winthrop

Total holiday rentals
Explore 60 holiday rentals in Winthrop

Nightly prices starting at
Winthrop holiday rentals start at ÂŁ30 per night before taxes and fees

Verified guest reviews
Over 6,170 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Winthrop holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winthrop rentals

4.8 Average rating
Winthrop stays are highly rated by guests â averaging 4.8 out of 5!

Nearby attractions
Winthropâs top spots include Orient Heights Station, Beachmont Station and Suffolk Downs Station
Destinations to explore
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- Waterfront rentals Winthrop
- Pet-friendly rentals Winthrop
- Rentals with a patio Winthrop
- Rentals with outdoor seating Winthrop
- Flat rentals Winthrop
- Rentals with a washing machine and dryer Winthrop
- Beachfront rentals Winthrop
- Rentals with a fireplace Winthrop
- Rentals with beach access Winthrop
- Family-friendly rentals Winthrop
- Fitness-friendly rentals Winthrop
- House rentals Suffolk County
- House rentals Massachusetts
- House rentals United States
- Hampton Beach
- Fenway Park
- Boston Common
- TD Garden
- Harvard University
- Revere Beach
- Brown University
- Lynn Beach
- New England Aquarium
- Duxbury Beach
- Good Harbor Beach
- Freedom Trail
- MIT Museum
- Canobie Lake Park
- Crane Beach
- Museum of Fine Arts, Boston
- Onset Beach
- Jenness State Beach
- Quincy Market
- Rye North Beach
- North Hampton Beach
- Prudential Center
- Roger Williams Park Zoo
- White Horse Beach




