Winchester Vacation Rentals from $180: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Winchester?

Modern 2BR Home Close to Campus & 10 min Boston : This vacation home rental outside of Winchester offers a selection of games, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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Our top choices for Winchester vacation rentals

1. Marriott Vacation Club® at Custom House, Boston

Downtown Boston

Frank

$305 nightly

Aug 30 - Aug 31

Total with taxes and fees

2. Crescent Suites Hotel

South Side

joseph

$161 nightly

Aug 12 - Aug 13

Total with taxes and fees

3. Kasa Boston at Fenway

Fenway–Kenmore

MARLYN

$350 nightly

Aug 3 - Aug 4

Total with taxes and fees

4. Maverick Suites at 245 Newbury St

Back Bay

Michael

$294 nightly

Aug 2 - Aug 3

Total with taxes and fees

Apartment | 1 bedroom, desk, laptop workspace, WiFi (free)

5. Furnished Apartments near Encore Boston

Everett

Warren

$272 nightly

Aug 2 - Aug 3

Total with taxes and fees

6. Maverick Suites at 28 Fenway

Fenway–Kenmore

LICHIEH

$259 nightly

Aug 12 - Aug 13

Total with taxes and fees

7. Maverick Suites at 40 Temple St

Beacon Hill

Rebecca

$263 nightly

Aug 2 - Aug 3

Total with taxes and fees

8. Enchanting Hidden Door Escape

Stoneham

$686 nightly

Aug 6 - Aug 7

Total with taxes and fees

9. Global Luxury Suites Downtown Boston

Chinatown

Neill

$299 nightly

Aug 16 - Aug 17

Total with taxes and fees

10. Maverick Suites at 400 Columbus Ave

South End

Evelyn

$217 nightly

Aug 12 - Aug 13

Total with taxes and fees

Premium Studio Suite | Premium bedding, desk, iron/ironing board, WiFi (free)

11. Charlesgate Suites

Fenway–Kenmore

timothy

$364 nightly

Aug 2 - Aug 3

Total with taxes and fees

Studio | Iron/ironing board, WiFi (free)

12. The Concord Hotel

South End

"The room was both well appointed and gorgeous. The location was just what I'd hoped for, enough city energy to feel the vibe but not so much that it lacked peace in the evening. Really cool neighborhood, close to restaurants doing high level cuisine. I had a question for the staff that was answered quickly and received a follow up to double check I had gotten what I needed. This is a spot worth revisiting."

Robert

$279 nightly

Aug 3 - Aug 4

Total with taxes and fees

1 Queen Bed with Sofa Bed (6th Floor - Elevator stops on 5th then stairs up) | Desk, iron/ironing board, WiFi (free), bed sheets

13. Temple Place Suites

Downtown Boston

Hunter

$172 nightly

Aug 12 - Aug 13

Total with taxes and fees

Premium Apartment | Living area | 24-inch Smart TV with digital channels

14. The Chester Hotel

South End

Shanida

$255 nightly

Aug 12 - Aug 13

Total with taxes and fees

Luxury Suite 3 | Living area | Smart TV, Netflix, Hulu, streaming services

15. The Monty Boston

Downtown Boston

Klaudia

$837 nightly

Aug 6 - Aug 7

Total with taxes and fees

Deluxe Double Room, Shared Bathroom | Iron/ironing board, WiFi (free), bed sheets

16. Premier Suites - Bay Village

Bay Village

Theresa

$171 nightly

Aug 12 - Aug 13

Total with taxes and fees

17. Luxury 2BR near Cambridge

Prospect Hill

Yonatan

18. Maverick Suites at 89 Marion

Coolidge Corner

Melissa

$255 nightly

Aug 3 - Aug 4

Total with taxes and fees

19. Furnished Apartment near BMC

South End

"I loved this apartment. It was perfect for what we needed. I only gave four stars because the apartment could use a little love and updating, and that may be important to some people. It was not for me. We were just over 2 miles away from Mass General where my husband was having an operation. It had a full kitchen, 1 1/2 baths, and was surprisingly quiet. The description of the apartment was clear there was no parking space associated with the apartment; however, I found that every night...

Christine

$301 nightly

Aug 2 - Aug 3

Total with taxes and fees

Suite (Luxury 1BR w/ King Bed & City Views) | Egyptian cotton sheets, premium bedding, down comforters

20. Symple Live

Fenway–Kenmore

Kimberley

$269 nightly

Aug 3 - Aug 4

Total with taxes and fees

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Top Winchester Hotel Reviews

Harborside Inn Of Boston

10/10 Excellent

"Great hotel. Staff and location were great. You will have to buy your own water and that was the only thing I would change."

Club Quarters Hotel Faneuil Hall, Boston

8/10 Good

"Really good location. Short walk from South Station; short walk to Opera House; and a fairly short walk to the North End. Room didn't have a fridge, but one was provided upon request, which was really nice for keeping leftovers from dinner and some wine! Would definitely stay here again!"

The Midtown Hotel MOD Collection by Sonesta

10/10 Excellent

"The best place to stay if you are visiting Boston with a car. We arrived really early at 9am and non of the rooms were available. We parked at the hotel parking lot, left our luggage in the car and started our day trip of Boston on foot. we came back to the hotel late afternoon after a full day walking around Boston. By that time, most of the rooms were already taken and we were forced to stay in an handicapped accessible room. The next morning the manager was extremely nice realizing that the room we checked in to was suitable for two guests on wheelchairs and not us, a couple celebrating their anniversary on a short get away vacation from NY. He said to me, "Your Anniversary night is on us, we are refunding the charges for your stay back to your credit card and please use this money for a nice good spa day on us" what an amazing hotel manager, The Midtown Hotel By Sonesta is lucky to have such a classic individual running the hotel. Highly recommended, thanks again"

Find out more about Winchester

Everything you need to know about Winchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $180 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winchester rentals

At Expedia, we put the best Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Winchester?

Yes, we have vacation rentals in Winchester close to Winter Pond, or you can choose a more remote option if you're looking for a relaxing stay. Winchester is known for its soccer matches and lake views.

What are some of the best vacation home rentals in Winchester?

Modern 2BR Home Close to Campus & 10 min Boston: This vacation home rental outside of Winchester offers a selection of games, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Winchester?

Choose from 3 Expedia vacation rentals in Winchester for a memorable vacation.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Winter Pond, or get outside and enjoy nature at Boston Common. TD Garden and Fenway Park are other popular places to visit in the area.

What are vacation rentals like in Winchester?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Winchester. Vacation rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.

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Check prices for these dates

Our top choices for Winchester vacation rentals

1. Marriott Vacation Club® at Custom House, Boston

2. Crescent Suites Hotel

3. Kasa Boston at Fenway

4. Maverick Suites at 245 Newbury St

5. Furnished Apartments near Encore Boston

6. Maverick Suites at 28 Fenway

7. Maverick Suites at 40 Temple St

8. Enchanting Hidden Door Escape

9. Global Luxury Suites Downtown Boston

10. Maverick Suites at 400 Columbus Ave

11. Charlesgate Suites

12. The Concord Hotel

13. Temple Place Suites

14. The Chester Hotel

15. The Monty Boston

16. Premier Suites - Bay Village

17. Luxury 2BR near Cambridge

18. Maverick Suites at 89 Marion

19. Furnished Apartment near BMC

20. Symple Live

Find vacation rentals that suit your style

Top Winchester Hotel Reviews

Harborside Inn Of Boston

Club Quarters Hotel Faneuil Hall, Boston

The Midtown Hotel MOD Collection by Sonesta

Omni Parker House

The Godfrey Hotel Boston

Hilton Boston Park Plaza

The Revolution Hotel

The Dagny Boston

Find out more about Winchester

Frequently asked questions

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