Title: Winthrop Vacation Home Rentals from CA $215: Search Top Private Vacation Homes for Rent | Expedia.ca

[Winthrop Travel Guide](https://expedia.ca/Winthrop.dx175875)[Hotels in Winthrop](https://expedia.ca/Winthrop-Hotels.d175875.Travel-Guide-Hotels)[Vacation Rentals in Winthrop](https://expedia.ca/Winthrop-Vacation-Rentals.d175875.Travel-Guide-VacationRentals)[Flights to Winthrop](https://expedia.ca/Cheap-Flights-To-Winthrop.d175875.Travel-Guide-Flights)[Winthrop Car Rentals](https://expedia.ca/Car-Rentals-In-Winthrop.d175875.Car-Rental-Guide)[Winthrop Vacation Packages](https://expedia.ca/Winthrop.d175875.Destination-Travel-Guides)

![Shot at sunrise from the Cottage Park Yacht Club parking lot towards the Winthrop Water tower. ](https://images.trvl-media.com/place/175875/55fc1560-9d93-4043-b5c7-3bb168feb877.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by mike s

# Winthrop Vacation Rentals

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## Check prices for these dates

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=175875&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=175875&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=175875&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=175875&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Winthrop vacation homes

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/125000000/124240000/124230300/124230263/c97c8bd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124240000/124230300/124230263/578fa007.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/125000000/124240000/124230300/124230263/c89df047.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124240000/124230300/124230263/a9fdbf4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Revere

[](https://www.expedia.ca/Boston-Hotels-Perfect-3-Bedroom-House-With-AC-In-Marvelous-Revere.h124230263.Hotel-Information)

CA $285

CA $404 total

includes taxes & fees

Dec 26 - Dec 27

[](https://www.expedia.ca/Boston-Hotels-Perfect-3-Bedroom-House-With-AC-In-Marvelous-Revere.h124230263.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/67000000/66850000/66847100/66847031/c6ab1483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66850000/66847100/66847031/8e9f1637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Bathroom](https://images.trvl-media.com/lodging/67000000/66850000/66847100/66847031/f822e23b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/67000000/66850000/66847100/66847031/479bdcb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Beacon Hill

[](https://www.expedia.ca/Boston-Hotels-Gorgeous-Beacon-Hills-Studio-Next-To-State-House.h66847031.Hotel-Information)

9.8/10

Exceptional

(31)

"As promised in listing, great location and property management team we will be back!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cathie B.

CA $245

CA $478 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Boston-Hotels-Gorgeous-Beacon-Hills-Studio-Next-To-State-House.h66847031.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106920000/106919400/106919387/bea226e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/107000000/106920000/106919400/106919387/c235c7a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106920000/106919400/106919387/d17a7467.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/107000000/106920000/106919400/106919387/e196fe57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Marblehead

[](https://www.expedia.ca/Boston-Hotels-NEW-2BR-Historic-Marblehead-HomeMinutes-To-Beach.h106919387.Hotel-Information)

10/10

Exceptional

(18)

"Enjoyed our stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mary D.

CA $180

CA $540 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Boston-Hotels-NEW-2BR-Historic-Marblehead-HomeMinutes-To-Beach.h106919387.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/92000000/91040000/91037000/91036903/367fea3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/92000000/91040000/91037000/91036903/w4320h3285x0y3-6304351e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels, toilet paper](https://images.trvl-media.com/lodging/92000000/91040000/91037000/91036903/6eb23938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91040000/91037000/91036903/2b2035e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Hyde Park

[](https://www.expedia.ca/Boston-Hotels-Lovely-Apartment-In-The-City-Of-Boston.h91036903.Hotel-Information)

9.6/10

Exceptional

(25)

"We were in town for a conference for work and didn't want to stay in a hotel. The place was very clean and smelled amazing. Perfect space 3 friends to stay. Host was great she answered when reaching out before the stay and the arrival was seamless."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

TIARA V.

CA $113

CA $448 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Boston-Hotels-Lovely-Apartment-In-The-City-Of-Boston.h91036903.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119600000/119591900/119591835/dc25e9a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119600000/119591900/119591835/cf94f7fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/120000000/119600000/119591900/119591835/3c2e9101.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119600000/119591900/119591835/39520f1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in North End

[](https://www.expedia.ca/Boston-Hotels-3BR3Bth-Entire-HouseSteps-To-Downtown-TD-Garden.h119591835.Hotel-Information)

10/10

Exceptional

(3)

"This place is so cool! Was incredibly clean, updated and offered all the amenities you need for a weekend get away. The location is wonderful as well with lots of markets, bakeries and restaurants all within walking distance. This is a must stay! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

mary j.

CA $370

CA $834 total

includes taxes & fees

Dec 30 - Dec 31

[](https://www.expedia.ca/Boston-Hotels-3BR3Bth-Entire-HouseSteps-To-Downtown-TD-Garden.h119591835.Hotel-Information)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/92000000/91890000/91883700/91883617/fdae0986.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91890000/91883700/91883617/26c85723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91890000/91883700/91883617/18f16ab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91890000/91883700/91883617/da72b451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bayside

[](https://www.expedia.ca/Hull-Hotels-Newly-Renovated-2-Br-Apt-1-Min-Walk-To-The-Beach-King-Queen.h91883617.Hotel-Information)

9.8/10

Exceptional

(15)

"Great property, clean, close to a baseball field which we loved. Super close to a beautiful beach that our kids enjoyed skim boarding and swimming in. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Candice C.

CA $233

CA $550 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Hull-Hotels-Newly-Renovated-2-Br-Apt-1-Min-Walk-To-The-Beach-King-Queen.h91883617.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113900000/113898600/113898567/ea77dad5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/114000000/113900000/113898600/113898567/afd662e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/114000000/113900000/113898600/113898567/61afdf75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113900000/113898600/113898567/decc6eed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Everett

[](https://www.expedia.ca/Boston-Hotels-2-Bedrooms-1-Bathroom-10-Min-AirportDowntown-Boston-7-Min-Encore-Casino.h113898567.Hotel-Information)

10/10

Exceptional

(5)

"Great neighborhood! House is beautiful and alot bigger then expected! If we ever get back to the area, this would be my first pick to stay. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Danielle s.

CA $222

CA $491 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Boston-Hotels-2-Bedrooms-1-Bathroom-10-Min-AirportDowntown-Boston-7-Min-Encore-Casino.h113898567.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/115000000/114170000/114164000/114163946/ef850f52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/115000000/114170000/114164000/114163946/25b3110a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114170000/114164000/114163946/w1318h979x1y19-315608be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/115000000/114170000/114164000/114163946/19bfc542.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Brockton

[](https://www.expedia.ca/Brockton-Hotels-Charming-Garden-Level-1-Bedroom-1-Bath-Apartment-In-Brockton.h114163946.Hotel-Information)

7.6/10

Good

(8)

"Easy to find, very comfortable, clean and convenient"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

David W.

CA $111

CA $215 total

includes taxes & fees

Jan 11 - Jan 12, 2026

[](https://www.expedia.ca/Brockton-Hotels-Charming-Garden-Level-1-Bedroom-1-Bath-Apartment-In-Brockton.h114163946.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/116000000/115980000/115977800/115977790/a9b43217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/116000000/115980000/115977800/115977790/73ef80e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/116000000/115980000/115977800/115977790/391131e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115980000/115977800/115977790/09b05f21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Nantasket Beach

[](https://www.expedia.ca/Boston-Hotels-Charming-2-Bedroom-Building-In-Delightful-Hull-With-Ocean-View.h115977790.Hotel-Information)

9.6/10

Exceptional

(5)

"Stayed with family for a wedding reception close by. Location is outstanding. Walkable to all the beach restaurants and beach. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah S.

CA $190

CA $381 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Boston-Hotels-Charming-2-Bedroom-Building-In-Delightful-Hull-With-Ocean-View.h115977790.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/123000000/122780000/122778600/122778535/b603d095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/123000000/122780000/122778600/122778535/e9b771a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122780000/122778600/122778535/9718a5e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/123000000/122780000/122778600/122778535/9f836916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Boston

[](https://www.expedia.ca/Boston-Hotels-Eagles-Landing-Logan-Airport.h122778535.Hotel-Information)

CA $129

CA $265 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Boston-Hotels-Eagles-Landing-Logan-Airport.h122778535.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/120000000/119630000/119628800/119628776/5b41d148.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119630000/119628800/119628776/1182d313.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/120000000/119630000/119628800/119628776/ab71ea45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119630000/119628800/119628776/3b11903d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in East Somerville

[](https://www.expedia.ca/Boston-Hotels-LUXE-4BDR2BA-Near-Boston-T-Station-Free-Parking.h119628776.Hotel-Information)

10/10

Exceptional

(2)

"Great stay and host was very responsive to any questions. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Matt R.

CA $156

CA $486 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Boston-Hotels-LUXE-4BDR2BA-Near-Boston-T-Station-Free-Parking.h119628776.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/112000000/111340000/111331300/111331262/004ca584.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111340000/111331300/111331262/7fe6e4e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/112000000/111340000/111331300/111331262/05076232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/112000000/111340000/111331300/111331262/7cec8d7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Dorchester

[](https://www.expedia.ca/Boston-Hotels-761-Spacious-4-Bedroom-Apartment-In-Charming-Boston.h111331262.Hotel-Information)

9.6/10

Exceptional

(14)

"Amazing location close to everything you are going to want to see in Boston, and great communication with the host."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Shane M.

CA $234

CA $571 total

includes taxes & fees

Dec 25 - Dec 26

[](https://www.expedia.ca/Boston-Hotels-761-Spacious-4-Bedroom-Apartment-In-Charming-Boston.h111331262.Hotel-Information)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/120000000/119140000/119138400/119138331/575dabbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, internet, bed sheets](https://images.trvl-media.com/lodging/120000000/119140000/119138400/119138331/f53a1c74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119140000/119138400/119138331/5f5eeead.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119138400/119138331/b340d629.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Quincy

[](https://www.expedia.ca/Boston-Hotels-Charming-3-Beds-In-2-Bedrooms-Apartment-Near-Quincy-Adams.h119138331.Hotel-Information)

10/10

Exceptional

(1)

"Nice amount of room and overall cleanliness."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jodi A.

CA $226

CA $388 total

includes taxes & fees

Jan 9 - Jan 10, 2026

[](https://www.expedia.ca/Boston-Hotels-Charming-3-Beds-In-2-Bedrooms-Apartment-Near-Quincy-Adams.h119138331.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/73000000/72590000/72583900/72583807/352e08d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72590000/72583900/72583807/39b46e36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/73000000/72590000/72583900/72583807/db6adb3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/73000000/72590000/72583900/72583807/d5f01cf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Quincy

[](https://www.expedia.ca/Boston-Hotels-383-Spacious-NEW-Townhouse-5-Beds-3-Baths-20To-Boston.h72583807.Hotel-Information)

9.6/10

Exceptional

(44)

"Beautiful home! Neighborhood is a little older, but the property is beautiful and close to Boston!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Christopher S.

CA $256

CA $581 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Boston-Hotels-383-Spacious-NEW-Townhouse-5-Beds-3-Baths-20To-Boston.h72583807.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/110000000/109120000/109118900/109118878/af33334c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109120000/109118900/109118878/963cdbb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109120000/109118900/109118878/43bde42d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/110000000/109120000/109118900/109118878/b37b282d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Marblehead

[](https://www.expedia.ca/Boston-Hotels-The-Sunset-Lighthouse-Marblehead-Exclusive-Waterfront-3brm25bath-Home.h109118878.Hotel-Information)

9.6/10

Exceptional

(15)

"Perfect location on Marblehead Neck with stunning views of the harbor. The house was just right for a family of 5 adults. We would come back and would recommend this lovely house to anyone. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Debbie B.

CA $281

CA $769 total

includes taxes & fees

Jan 14 - Jan 15, 2026

[](https://www.expedia.ca/Boston-Hotels-The-Sunset-Lighthouse-Marblehead-Exclusive-Waterfront-3brm25bath-Home.h109118878.Hotel-Information)

![House](https://images.trvl-media.com/lodging/118000000/117740000/117735900/117735808/66d607dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/118000000/117740000/117735900/117735808/fb73a716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/118000000/117740000/117735900/117735808/7f7e58bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/118000000/117740000/117735900/117735808/eb1f2b1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Billerica

[](https://www.expedia.ca/Boston-Hotels-Lakeview-Getaway-With-Hot-Tub.h117735808.Hotel-Information)

CA $371

CA $922 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/Boston-Hotels-Lakeview-Getaway-With-Hot-Tub.h117735808.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/109000000/108240000/108237500/108237439/67c5ea68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108240000/108237500/108237439/24bfbb3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/109000000/108240000/108237500/108237439/314861fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/109000000/108240000/108237500/108237439/e71ec9fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Salem

[](https://www.expedia.ca/Boston-Hotels-Entire-4BR-2-Bath-Home-L-Minutes-To-Downtown-Salem.h108237439.Hotel-Information)

10/10

Exceptional

(18)

"The house was clean and close to everything!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Stephanie D.

CA $270

CA $695 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Boston-Hotels-Entire-4BR-2-Bath-Home-L-Minutes-To-Downtown-Salem.h108237439.Hotel-Information)

![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/104000000/103820000/103810900/103810819/w1280h847x2y0-8f7354be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103820000/103810900/103810819/w1280h839x2y0-ef281ffa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/104000000/103820000/103810900/103810819/w1280h853x2y0-e4c002c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cookware/dishes/utensils](https://images.trvl-media.com/lodging/104000000/103820000/103810900/103810819/w1280h846x2y0-8cece9f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Dorchester

[](https://www.expedia.ca/Boston-Hotels-Cozy-3-Bedroom-Free-Parking.h103810819.Hotel-Information)

10/10

Exceptional

(1)

"The space was great! Exactly what we needed as coworkers travelling for a conference. Host was very communicative, the place was clean and safe, and the beds were very comfortable. Would recommend to anyone!"

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Melissa S.

CA $234

CA $621 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Boston-Hotels-Cozy-3-Bedroom-Free-Parking.h103810819.Hotel-Information)

![Smart TV](https://images.trvl-media.com/lodging/73000000/72590000/72584600/72584577/07776021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/73000000/72590000/72584600/72584577/d038ed64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/73000000/72590000/72584600/72584577/4c656016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/73000000/72590000/72584600/72584577/5b4932fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Quincy

[](https://www.expedia.ca/Boston-Hotels-37-Greater-Boston-Cozy-Townhouse.h72584577.Hotel-Information)

9.2/10

Wonderful

(36)

"property was as described, very clean and remodeled. Owner was a pleasure to deal with. Would stay again in the future. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andrew A.

CA $171

CA $479 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Boston-Hotels-37-Greater-Boston-Cozy-Townhouse.h72584577.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/73000000/72590000/72584000/72583990/f46acbda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72590000/72584000/72583990/cdc94e65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72590000/72584000/72583990/4a680a88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/73000000/72590000/72584000/72583990/5be50117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Quincy

[](https://www.expedia.ca/Boston-Hotels-39-Newly-Built-Townhouse.h72583990.Hotel-Information)

9.6/10

Exceptional

(50)

"Very clean and stay was enjoyable. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sheldon S.

CA $248

CA $572 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](https://www.expedia.ca/Boston-Hotels-39-Newly-Built-Townhouse.h72583990.Hotel-Information)

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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## Find vacation rentals that suit your style

Aparthotels

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Apartments

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Villas

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Condos

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Private vacation homes

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Winthrop%2C+Massachusetts%2C+United+States+of+America&regionId=175875&latLong=42.377819%2C-70.981132&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=COTTAGE)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Winthrop%2C+Massachusetts%2C+United+States+of+America&regionId=175875&latLong=42.377819%2C-70.981132&adults=2&startDate=2026-03-24&d1=2026-03-24&endDate=2026-03-27&d2=2026-03-27&lodging=HOUSE_BOAT)

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## Top Winthrop Hotel Reviews

![The Godfrey Hotel Boston](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg)

### The Godfrey Hotel Boston

10/10 Excellent

"Great room; amazing location - walking distance to almost anything and very close to the T. Ruka and the coffee shop were both awesome. "

[](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information)

![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg)

### Encore Boston Harbor

10/10 Excellent

"I didn’t get a chance to have breakfast "

[](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information)

![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg)

### Harborside Inn Of Boston

10/10 Excellent

"Great staff"

[](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information)

![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg)

### The Dagny Boston

10/10 Excellent

"The room and the common"

[](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information)

![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/c414a1f3_y.jpg)

### Omni Parker House 

10/10 Excellent

"Wow what an amazing stay! From checking in the amazing concierge made sure I was able to check in early. I was greeted by my first name the rest of my trip the hotel bar that was connected the last hurrah I went to every night before dinner. I had an amazing waiter Francesco I sat with the three nights in a row. He was very attentive made sure I was knowledgeable of the menu.I was traveling alone and as woman it was great to feel safe. The room was cozy and I loved the updated features to such an historical building. The location was perfect, walking distance to everything. I will definitely be coming back. "

[](https://expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information)

![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg)

### citizenM Boston Back Bay

10/10 Excellent

"Ahh good"

[](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information)

![The Revolution Hotel](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg)

### The Revolution Hotel

10/10 Excellent

"My room was great and the bed was so comfortable! The bathrooms were consistently cleaned and I had a wonderful experience overall. Would definitely book again!"

[](https://expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information)

![The Arcadian Hotel](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/f8ad7683_y.jpg)

### The Arcadian Hotel

10/10 Excellent

"Nice , modern hotel unfortunately without a restaurant "

[](https://expedia.ca/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.Hotel-Information)

![The Westin Copley Place, Boston, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/10000/4500/4443/ac4901eb_y.jpg)

### The Westin Copley Place, Boston, a Marriott Hotel

10/10 Excellent

"Large, comfortable room."

[](https://expedia.ca/Boston-Hotels-The-Westin-Copley-Place.h4443.Hotel-Information)

## Find out more about Winthrop

## Winthrop Vacation Homes information

| Number of reviews | 284                |
| ----------------- | ------------------ |
| Accommodation     | 598 Vacation Homes |
| Lowest Price      | CA $215            |
| Highest Price     | CA $922            |

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- [Flights from Chicago (ORD) to Boston (BOS) ](https://www.expedia.ca/lp/flights/ord/bos/chicago-to-boston)
- [Flights from Philadelphia (PHL) to Boston (BOS) ](https://www.expedia.ca/lp/flights/phl/bos/philadelphia-to-boston)
- [Flights from Seattle (SEA) to Boston (BOS) ](https://www.expedia.ca/lp/flights/sea/bos/seattle-to-boston)
- [Flights from Syracuse (SYR) to Boston (BOS) ](https://www.expedia.ca/lp/flights/syr/bos/syracuse-to-boston)
- [Flights from Edmonton (YEG) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yeg/bos/edmonton-to-boston)
- [Flights from Fredericton (YFC) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yfc/bos/fredericton-to-boston)
- [Flights from Kingston (YGK) to Boston (BOS) ](https://www.expedia.ca/lp/flights/ygk/bos/kingston-to-boston)
- [Flights from Hamilton (YHM) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yhm/bos/hamilton-to-boston)
- [Flights from Halifax (YHZ) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yhz/bos/halifax-to-boston)
- [Flights from Kitchener (YKF) to Boston (BOS) ](https://www.expedia.ca/lp/flights/ykf/bos/kitchener-to-boston)
- [Flights from Kelowna (YLW) to Boston (BOS) ](https://www.expedia.ca/lp/flights/ylw/bos/kelowna-to-boston)
- [Flights from Ottawa (YOW) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yow/bos/ottawa-to-boston)
- [Flights from Québec (YQB) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yqb/bos/quebec-to-boston)
- [Flights from Windsor (YQG) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yqg/bos/windsor-to-boston)
- [Flights from Moncton (YQM) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yqm/bos/moncton-to-boston)
- [Flights from Regina (YQR) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yqr/bos/regina-to-boston)
- [Flights from Thunder Bay (YQT) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yqt/bos/thunder-bay-to-boston)
- [Flights from Saint John (YSJ) to Boston (BOS) ](https://www.expedia.ca/lp/flights/ysj/bos/saint-john-to-boston)
- [Flights from Toronto (YTZ) to Boston (BOS) ](https://www.expedia.ca/lp/flights/ytz/bos/toronto-to-boston)
- [Flights from Montreal (YUL) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yul/bos/montreal-to-boston)
- [Flights from Vancouver (YVR) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yvr/bos/vancouver-to-boston)
- [Flights from Winnipeg (YWG) to Boston (BOS) ](https://www.expedia.ca/lp/flights/ywg/bos/winnipeg-to-boston)
- [Flights from Saskatoon (YXE) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yxe/bos/saskatoon-to-boston)
- [Flights from London (YXU) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yxu/bos/london-to-boston)
- [Flights from Calgary (YYC) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yyc/bos/calgary-to-boston)
- [Flights from Charlottetown (YYG) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yyg/bos/charlottetown-to-boston)
- [Flights from Victoria (YYJ) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yyj/bos/victoria-to-boston)
- [Flights from St. John's (YYT) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yyt/bos/st-johns-to-boston)
- [Flights from Toronto (YYZ) to Boston (BOS) ](https://www.expedia.ca/lp/flights/yyz/bos/toronto-to-boston)

- [Visit Orient Heights ](https://www.expedia.ca/Boston-Orient-Heights.dx142091)
- [Revere Beach ](https://www.expedia.ca/Revere-Beach-Boston.d6171946.Vacation-Attraction)

- [Rental cars Logan Intl. airport ](https://www.expedia.ca/Car-Rentals-In-Logan-Intl.d5459778.Car-Rental-Guide)
- [Car rentals near Orient Heights ](https://www.expedia.ca/Car-Rentals-In-Orient-Heights.d142091.Car-Rental-Guide)

- [Things to do in Boston ](https://www.expedia.ca/Things-To-Do-In-Boston.d178239.Travel-Guide-Activities)

- [Book Vacation Homes in Winthrop on Expedia.com ](https://www.expedia.com/Winthrop-Private-Vacation-Homes.d175875-aaPrivateVacationHomes.Travel-Guide-Accommodation)