Apartment vacation rentals in Winthrop

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Popular amenities for Winthrop apartment rentals

Weekly apartment rentals

Superhost
Apartment in Chelsea
4.8 out of 5 average rating, 30 reviews

Boston Modern Apt: Luxe Stay w/ Gym, Parking

ShuRating, 5 stars1 week ago
Stephanie’s 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!
Guest favorite
Apartment in Winthrop
4.9 out of 5 average rating, 77 reviews

Vibrant Winthrop Apartment - Close to Ocean!

DylanRating, 5 stars3 weeks ago
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!😊😌
Top guest favorite
Apartment in Winthrop
4.97 out of 5 average rating, 64 reviews

Pleasant Place 2

AndrewRating, 5 stars1 day ago
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 couldn’t have asked for more. We will definitely be back next time we are in the area.
Top guest favorite
Apartment in Hull
5 out of 5 average rating, 60 reviews

Cozy Coastal Apt w/ Ocean View Patio & Fireplace

AmeliaRating, 5 stars2 weeks ago
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!!
Guest favorite
Apartment in Revere
4.94 out of 5 average rating, 33 reviews

New England Charm - Minutes From Boston

BeccaRating, 5 stars6 days ago
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!!!
Guest favorite
Apartment in Hull
4.96 out of 5 average rating, 81 reviews

Coastal Home Walk to Beach

AndreasRating, 5 stars1 week ago
We had a lovely stay at Catherine’s quaint home. The space is very clean and we had zero issues during our stay, we would love to come back!
Top guest favorite
Apartment in Winthrop
4.86 out of 5 average rating, 21 reviews

Charming condo steps from beach

SandraRating, 5 stars5 days ago
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.
Guest favorite
Apartment in Revere
4.91 out of 5 average rating, 43 reviews

Peaceful Top-floor Condo Near Beach

TaraRating, 5 stars2 days ago
Absolutely loved staying here! Luis’ 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

Top guest favorite
Apartment in Salem
4.98 out of 5 average rating, 386 reviews

Winter Island Retreat

MorganRating, 5 stars1 week ago
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.
Guest favorite
Apartment in East Boston
5 out of 5 average rating, 23 reviews

1Bedroom • Boston• Airport • Magnificent view

PeterRating, 5 stars4 days ago
Emma’s 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.
Guest favorite
Apartment in Roxbury
4.97 out of 5 average rating, 348 reviews

Light-Filled Luxury Apartment with View

NataliaRating, 5 stars1 week ago
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.
Superhost
Apartment in Dorchester
4.83 out of 5 average rating, 218 reviews

🎖The Ashmont Apartment | Close to Subway/Downtown

ColleenRating, 5 stars2 days ago
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.
Superhost
Apartment in Revere
4.82 out of 5 average rating, 77 reviews

Chic/Cozy2BR-nearAirport & Beach

JobRating, 5 stars1 week ago
The stay met our expectations; we didn’t 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.
Top guest favorite
Apartment in Salem
5 out of 5 average rating, 22 reviews

NEW Spacious 1BR w/Parking in the Heart of Salem

JamesRating, 5 stars6 days ago
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.
Top guest favorite
Apartment in Salem
5 out of 5 average rating, 26 reviews

Beautiful Place to Stay In Salem

LuluRating, 5 stars2 weeks ago
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!
Top guest favorite
Apartment in Salem
4.96 out of 5 average rating, 868 reviews

Your home for the holidays!

KarlaRating, 5 stars4 days ago
Edgar’s 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

Guest favorite
Apartment in South Boston
4.91 out of 5 average rating, 66 reviews

South Boston. Minutes away from Convention Center

LeeRating, 5 stars2 weeks ago
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!
Guest favorite
Apartment in Woburn
4.94 out of 5 average rating, 153 reviews

Your Cozy 1 BR Apt & Relaxing Retreat

EarlRating, 5 stars1 day ago
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 Arancini’s. “Wicked” close to Boston. If needing to come back to the area I will seek out this again !!
Guest favorite
Apartment in Revere
4.85 out of 5 average rating, 13 reviews

Step Into Spacious Vintage Charm in West Revere

LindaRating, 5 stars1 week ago
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!
Apartment in Greater Mattapan
4.67 out of 5 average rating, 3 reviews

Georges families

TpotRating, 5 stars1 month ago
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!
Superhost
Apartment in Cambridge
4.87 out of 5 average rating, 38 reviews

Central Square Upscale Penthouse near MIT/Harvard

MichaelRating, 5 stars4 weeks ago
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
Guest favorite
Apartment in Arlington
4.98 out of 5 average rating, 196 reviews

Lakeside apartment, patio, hot tub, outside shower

PietroRating, 5 stars2 weeks ago
Everything was absolutely exceptional! My parents stayed here for two weeks and had a wonderful experience. The hosts were incredibly kind and responsive — 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!
Apartment in Nahant
4.51 out of 5 average rating, 134 reviews

Beach Home with Jacuzzi and Direct Ocean Access

RowanRating, 5 stars2 days ago
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!
Top guest favorite
Apartment in North End
5 out of 5 average rating, 45 reviews

Amazing Location in Little Italy with Roof Deck

NancyRating, 5 stars1 month ago
Beautiful condo, perfect for 2 people! Everything you need was provided. Deck was lovely. The location can’t be beat. Highly recommend for a Fun Boston Experience!

Quick stats about apartment rentals in Winthrop

  • Total rentals

    100 properties

  • Nightly prices starting at

    ﺩ.ﺇ147 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

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  5. Winthrop
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