
Apartment vacation rentals in Winthrop
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Top-rated apartment rentals in Winthrop
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Popular amenities for Winthrop apartment rentals
Weekly apartment rentals

Boston Modern Apt: Luxe Stay w/ Gym, Parking
Stephanieâs place is beautiful and matches exactly as she listed. The location is very convenient when we visited Boston the past week. Stephanie is also very friendly and proactive about instructions. Highly recommend. Thank you for your hospitality and sharing your beautiful home Stephanie!

Vibrant Winthrop Apartment - Close to Ocean!
Would absolutely stay here again next time I come to Massachusetts. Super comfortable and snacks and seltzers available were a touch of how thoughtful they are about their customers!đđ

Pleasant Place 2
We had a wonderful long weekend at the rental. Beautiful area. Lots to do close by and only about 20 min to most attractions in Boston. The apartment was clean and comfortable and we couldnât have asked for more. We will definitely be back next time we are in the area.

Cozy Coastal Apt w/ Ocean View Patio & Fireplace
We really loved this spacious studio. The landscaping was so beautiful it really added to the experience and a sweet family of bunnies were hopping in front of the windows. The bed is very comfortable and the giant TV was very nice too. We sat on the couch and looked out at the ocean and filled our days with trips to the beach, playground, and local restaurants. It was a fun little staycation that we will most likely book again!!

New England Charm - Minutes From Boston
The space was just perfect for us! Walgreens across the street, bakery on the next block, and lots of restaurants close by. Comfy beds, lots of towels, well equipped kitchen and coffee provided!! Perfect hub for going to Boston, Salem and Provincetown. We would definitely stay again!!!

Coastal Home Walk to Beach
We had a lovely stay at Catherineâs quaint home. The space is very clean and we had zero issues during our stay, we would love to come back!

Charming condo steps from beach
My cousin and I were visiting family in Winthrop and were lucky to fine this lovely Airbnb. It was immaculate and the decorating was beautiful. The kitchen has everything you would ever need and this flat was roomy and very comfortable. It was one block to the beach and close to a good restaurant and a wonderful Ice cream parlor. Hope to stay here again on our next visit. Also want to mention that Casie was easy to contact for questions and very nice.

Peaceful Top-floor Condo Near Beach
Absolutely loved staying here! Luisâ place was exactly what we needed, and perfectly as described. It was a very nice, quiet neighborhood and a super easy walk to the private beach. It was very convenient to our Boston excursions as well. The bed was super comfy, and the entire space was very clean and well maintained. The kitchen was well stocked and had everything we could possibly need. I loved all the little details, even down to the coordinating silverware, dishes and cookware. We will most definitely stay here again if we come back to the Boston area!
Private apartment rentals

Winter Island Retreat
Our stay at Dave's place on Winter Island was spectacular! The photos do not do justice for the views. The yard is beautiful and well-kept, and my favorite part was sitting on the porch with my coffee each morning. Inside is cozy, but perfect for two guests. Dave has all you'll need in the kitchen and bathroom, which was a bonus! We traveled from New Mexcio, and it was a long ways, but I would absolutely stay at Dave's place again if we come back to the area. You won't find a better accommodation, and at this price, just amazing. So grateful I was able to bring my daughter for such an incredible stay in Salem.

1Bedroom ⢠Boston⢠Airport ⢠Magnificent view
Emmaâs place was great for our stay in Boston. Super convenient to the blue line! Also make sure to hit up Melodias just a short walk from the place for some great food and music.

Light-Filled Luxury Apartment with View
Wonderful one of a kind studio in a very old beautiful house. Plenty of room, lots of light, modern appliances. I enjoyed every minute of it.

đThe Ashmont Apartment | Close to Subway/Downtown
This spot was very comfortable, clean and beautiful just as the photos show! We appreciated all the extras included and the lovely outdoor setting was the icing on the cake! The hosts were very great to deal with and we would recommend to anyone travelling to Boston. The transit is a short walk from the home so the location worked for us. We would love to return and would surely look at staying again.

Chic/Cozy2BR-nearAirport & Beach
The stay met our expectations; we didnât plan to spend much time at the house, except to sleep. The neighborhood is close to the beach with a lot of great food options and things to do near by. The host has some info on things to do in the area. Overall very good and would stay here again. Home is Very Clean and to our expectations. Generally felt like a Safe area and Quiet neighbors, no one bothered us.

NEW Spacious 1BR w/Parking in the Heart of Salem
If you are looking for a home with historic colonial charm within walking distance to all that Salem has to offer, this is it. This two-story apartment is located directly on the Salem Commons. We appreciated the large upstairs bedroom with its king-size bed, separate dressing room and large bathroom with huge shower. The adorable living room was a wonderful gathering space. You could hear the faint sound of children in the small playground across the street, but everything became quiet around dinner time. Although we didn't do any cooking, we appreciated the large, fully-equipped kitchen for heating up leftovers. The apartment is in a multi-family home that shares a large, shady outdoor patio with a well-tended garden. Rachel provided a detailed guidebook with all of the information that we needed, including videos, and she responded very quickly to any additional correspondence that we had. We would highly recommend this home to anyone who is visiting Salem.

Beautiful Place to Stay In Salem
This was exceptional. Becky's AirBnB is absolutely STUNNING!!! I think, quite honestly, it was the most beautiful accommodation I've ever stayed in. Becky thought of EVERYTHING, from the delightful snacks and beverages, to the notebook of fabulous restaurant and activity recommendations, plus the elegant and soothing seaside decor! Some of the plusses include a cozy gas fireplace, a great gas range to cook on, and an outdoor grill! We cooked up and grilled up some fabulous feasts during our stay! But the real treasure here is Becky herself. Although she grew up in Salem, she says she inherited her mama's Southern hospitality, and it definitely shows! She is warm and joyful, and my daughters and I feel we have made fast friends with her. We truly look forward to visiting Becky again!

Your home for the holidays!
Edgarâs home had everything we needed. The beds were super comfortable. The AC was cold and the curtains allowed us to sleep in.
Apartment rentals with a hot tub

South Boston. Minutes away from Convention Center
The apartment was exactly like described in an amazing location. I was attending a conference at the EXPO center, and it was an easy 25 minute walk there and back. Area is safe and clean. The best feature is the is less than a minute walk from a beautiful park and beach. Multiple Restaurants within walking distance and had no trouble getting items delivered. Would definitely stay again. Thank you so much Tanya!

Your Cozy 1 BR Apt & Relaxing Retreat
Beautiful accommodations. Very comfy. Love the hot tub. Woburn ( pronounced WooBun lol ) is such a cute little hamlet. Good restaurants in walking distance. Strongly recommend Aranciniâs. âWickedâ close to Boston. If needing to come back to the area I will seek out this again !!

Step Into Spacious Vintage Charm in West Revere
Our stay was wonderful, everything was very clean and cozy. We had plenty of room for our group and was very convenient going to and from Boston for all of our activities. The host(s) were quick to respond to any questions or concerns we had. Thank you!

Georges families
I enjoyed my stay here, I had trouble parking and the host was extremely responsive and offered to even let me stay in their driveway. I had no issues and I was very happy with the space I had!

Central Square Upscale Penthouse near MIT/Harvard
The unit we rented ended up not being available at the last moment but Jonah was able to find and arrange comparable accommodation set away

Lakeside apartment, patio, hot tub, outside shower
Everything was absolutely exceptional! My parents stayed here for two weeks and had a wonderful experience. The hosts were incredibly kind and responsive â they replied to our messages and requests immediately, which made everything so easy and stress-free. My parents left extremely happy and are already talking about coming back. Highly recommended!

Beach Home with Jacuzzi and Direct Ocean Access
This place is an amazing spot for anyone looking for a beach getaway. You can walk to just about anywhere in Nahant within 10-15 minutes, including a few different beaches. The perfect spot to be able to take full advantage of some free time!

Amazing Location in Little Italy with Roof Deck
Beautiful condo, perfect for 2 people! Everything you need was provided. Deck was lovely. The location canât be beat. Highly recommend for a Fun Boston Experience!
Quick stats about apartment rentals in Winthrop
Total rentals
100 properties
Nightly prices starting at
ﺊ.ďş147 before taxes and fees
Total number of reviews
4.7K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
10 properties have a pool
Destinations to explore
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- Hampton Beach
- Boston Common
- Fenway Park
- Revere Beach
- TD Garden
- Harvard University
- Lynn Beach
- Brown University
- Duxbury Beach
- North Hampton Beach
- New England Aquarium
- Sagamore Beach
- Faneuil Hall Marketplace
- Freedom Trail
- Canobie Lake Park
- Crane Beach
- Sandwich Glass Museum
- Good Harbor Beach
- Prudential Center
- Roger Williams Park Zoo
- MIT Museum
- Rye North Beach
- Museum of Fine Arts, Boston
- Quincy Market