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Compare 509 Vacation Homes in Winthrop with updated reviews, rates, and availability.

OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths

9.6 out of 10, Exceptional, (9)
"Loved this old historic home and the town. Had everything we needed to make our stay comfortable. Would love to come back again! Everything was walkable. Charming town. Gorgeous ocean all around. In love!"
OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths

Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV

10.0 out of 10, Exceptional, (1)
"We had an incredible experience staying at this property! The house was absolutely beautiful and exceeded our expectations. It was clean, well-maintained, and had everything we needed for a comfortable and relaxing stay. My family loved it so much, and we're already planning to come back in the future. Thank you to our wonderful host for making this stay so memorable!"
Villa in Boston 6BR 5.5 Bath-IGLOO, Arcade, Parking,Game Room,EV

Centrally located in the heart of Boston near T

8.8 out of 10, Excellent, (15)
"Enjoyed this little place so much. Very safe neighborhood! "
The price is AED 643
AED 1,642 total
includes taxes & fees
6 Jan - 7 Jan
Centrally located in the heart of Boston near T

5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

10.0 out of 10, Exceptional, (123)
"The house is located on a quite street near a quaint Downtown Area The house has area for two cars The house was immaculate and very comfortable. The owner Gregg was very welcoming and worked hard to make sure everything was Ok I want to thank him again for letting my family stay in such a beautiful home If you need a place do not hesitate to take this house "
The price is AED 1,194
AED 2,158 total
includes taxes & fees
6 Jan - 7 Jan
5-bedroom house. Close to airport, bus & train. 10 min from Boston. Sleeps 10.

Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC

10.0 out of 10, Exceptional, (3)
"This place was so peaceful and relaxing "
Beach-view home with beach access, deck, grill, washer/dryer, 2 kayaks, & AC

6 bedroom house in a quiet and convenient neighborhood

6.8 out of 10, (3)
"The good, Large House, lots of bedrooms. Felt very safe, nice Alarm system. And the Piano was very fun for a singing and having fun. Reconstruction in process. The bad, the beds, not good, the house is falling apart, scary stairs, the bath rooms are tiny and do not offer shampoo, conditioner, and conditioner. Could not find bath towels. The ugly - mouse droppings all over the kitchen. Mouse found in one bedroom, captured mouse and took outside. Let host know that there was a mouse and mice...
6 bedroom house in a quiet and convenient neighborhood

Dog-friendly, spacious coastal retreat with large deck & W/D - walk to beaches

8.0 out of 10, Very Good, (7)
"This house is spacious great living area for family get away. Location is fabulous!"
Dog-friendly, spacious coastal retreat with large deck & W/D - walk to beaches

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

9.6 out of 10, Exceptional, (108)
"It was the best location, just a VERY short walk to all that Salem has to offer! It is right across the street from Jaho, which is an amazing coffee place and access to the lighthouse is directly across the street. The layout of the unit is awesome - the primary is in the basement with its own living area, HUGE walk-in closet, and bathroom, while the two other bedrooms are on the main floor. It felt very private having the whole basement to ourselves. The only downside (and it's a personal...
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Harvard House Host Your 2024 Family Gathering In Boston at This Beautiful Venue

9.8 out of 10, Exceptional, (62)
"Once again, we are so appreciative of all the comfortable first-floor spaces to spread out as a family. The kitchen is equipped to produce a fully home-prepared feast—all the utensils, pots, pans, knives, and dishes you might need. The dining room table can comfortably accommodate a very large group. Cozy beds, extra blankets as needed, and loads of towels. The host is very communicative and caring."
Harvard House Host Your 2024 Family Gathering In Boston at This Beautiful Venue

Remodeled Townhouse close to Boston

10.0 out of 10, Exceptional, (23)
"Our family of four enjoyed a very comfortable stay while visiting relatives near Watertown. The beds were comfortable and everything worked well. Our host responded to any questions very promptly. The place is a few minutes’ walking distance to restaurants and a drug store, and a nice walk along the River. It’s near a busy street and was noisy in the weekday morning but earplugs can cover that. Recommended!"
Remodeled Townhouse close to Boston

Newly renovated home, top of the line appliances.

9.8 out of 10, Exceptional, (111)
"We spent Thanksgiving weekend with our adult child at the house, and what a great place it was. The house had everything we needed, including a wonderful kitchen for cooking Thanksgiving dinner. And the price was competitive with what it would have cost for a hotel for just us. We will consider this place for our next Boston visit."
Newly renovated home, top of the line appliances.

Stunning Beach Cottage just steps from Marblehead Harbor and Town

10.0 out of 10, Exceptional, (42)
"Everything about our stay was terrific! The house is old and feels historical, but it's also renovated and has all the modern amenities. It's comfortable and quiet and perfect for relaxing, cooking and enjoying time with the people you love. And it's just a short walk to the ocean and some great local Marblehead shops and restaurants. It is also a quick drive over to Salem, which was great. We also drove up to New Hampshire and Maine for a day trip, and that was a quick drive up as well....
Stunning Beach Cottage just steps from Marblehead Harbor and Town

MODERN Spacious 4bed 2bath HARVARD MIT BOS Cambridge Somerville walk everywhere!

9.4 out of 10, Exceptional, (44)
"The stay was in suburb of Boston. Good location. There was a few repairs needed. Bathroom sink faucet moved. There was a light in bedroom ceiling that had open wires. Other than that the place was clean. The outside patio could used cleaned up but we didn’t ise"
The price is AED 951
AED 1,965 total
includes taxes & fees
6 Jan - 7 Jan
MODERN Spacious 4bed 2bath HARVARD MIT BOS Cambridge Somerville walk everywhere!

Norwood Luxe Suite- Pet friendly & Commuter friendly

10.0 out of 10, Exceptional, (8)
"We had additional work to complete in Sharon, MA on a remodel project that we extended another week at Norwood for our team members, which offered them a place to unwind and recharge after long hours working. Norwood is lovely, clean and well-equipped with all the amenities. Susan is such an attentive host, it made for an all around wonderful experience. "
Norwood Luxe Suite- Pet friendly & Commuter friendly

Charming Scituate Home w/ Deck - Walk to Beaches!

9.6 out of 10, Exceptional, (11)
"The property was clean and neat and the house furnishings were very eclectic. The kitchen table only seats three, but if you are there in the summer there are plenty of tables and chairs outside on the deck. Nice view to the water but no beach at the end of the road. We were there in late November and there was no heat in the kitchen and in one of the bedrooms. If you are over 5’9” you cannot stand up straight in the bathrooms, as the ceilings are very low. My husband is 6’4” tall, so that was...
Charming Scituate Home w/ Deck - Walk to Beaches!

Unique Scituate Vacation Rental on Herring River!

10.0 out of 10, Exceptional, (13)
"We rented this home for family coming in for the holidays and it exceeded our expectations. The location was perfect, the house was perfect and we would 10000% rent again!"
Unique Scituate Vacation Rental on Herring River!

Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

NEW Tiny House Walk to Essex Main St+Boat Launch

10.0 out of 10, Exceptional, (4)
"Perfect location, quiet, clean and comfortable! Would recommend! We enjoyed being so close to our family in Ipswich and Hamilton. Thank you!!"
NEW Tiny House Walk to Essex Main St+Boat Launch

76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston

The price is AED 584
AED 1,490 total
includes taxes & fees
6 Jan - 7 Jan
76/1 - SPRING GETAWAY 10% OFF! Spacious 4-bedroom apartment in charming Boston

Peaceful 2Br House in Cambridge

2.0 star property
6.0 out of 10, (4)
"A marvelous place. Parking spot was appeciated!"
Peaceful 2Br House in Cambridge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Winthrop

Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

10.0 out of 10, Exceptional, (39)
"My sister and I did a trip where we split a day in Boston and a day in Salem. This was a perfect place to stay for both. Frank was a lovely host who was very responsive and gave us a lot of good suggestions. We especially really enjoyed getting to use the balcony. My sister and I both said we would love to stay here again! "
Casa de Los Clarey Boston Airport Beaches Off Street Parking Available

Sonder 907 Main

4.0 star property
8.2 out of 10, Very Good, (410)
"Perfect location!"
The price is AED 434
AED 503 total
includes taxes & fees
30 Jan - 31 Jan
Sonder 907 Main

Maverick Suites at 28 Fenway

3.0 star property
9.0 out of 10, Wonderful, (158)
"Great stay. "
The price is AED 474
AED 904 total
includes taxes & fees
11 Jan - 12 Jan
Maverick Suites at 28 Fenway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.