Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Charming 2-bedroom building in delightful Hull with ocean view

10.0 out of 10, Exceptional, (2)
"Great place to stay we had a great time the host was awesome and easy to communicate with thank you for a wonderful weekend"
The price is €351
includes taxes & fees
13 Jul - 14 Jul
Charming 2-bedroom building in delightful Hull with ocean view

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

2.0 star property
9.8 out of 10, Exceptional, (8)
"We had a lovely weekend! The views were beautiful and the location was great for our day trips. We will definitely be looking to rebook! "
The price is €727
includes taxes & fees
13 Jul - 14 Jul
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

NEW 2BR Historic Marblehead Home+Minutes to Beach

2.0 star property
10.0 out of 10, Exceptional, (7)
"My family stayed in October for a quick weekend getaway. Great location and easy to get to from Boston. Would definitely book again. "
The price is €351
includes taxes & fees
13 Jul - 14 Jul
NEW 2BR Historic Marblehead Home+Minutes to Beach

Rockmere Inn

3.5 star property
Rockmere Inn

Downtown Marblehead 2brm/1.5bath w/ deck

10.0 out of 10, Exceptional, (1)
"The property was large with lots of natural light. Very clean and fully stocked for the stay."
Downtown Marblehead 2brm/1.5bath w/ deck

Bright & Stylish 2BD/1BA in Town Center w Parking!

10.0 out of 10, Exceptional, (16)
"Definitely will be staying there again!"
The price is €344
includes taxes & fees
5 Aug - 6 Aug
Bright & Stylish 2BD/1BA in Town Center w Parking!

Prime location in town w parking! Walk to beach, shops & harbor-Sleeps 8

10.0 out of 10, Exceptional, (14)
"Property as advertised. Great walkable location"
The price is €783
includes taxes & fees
11 Aug - 12 Aug
Prime location in town w parking! Walk to beach, shops & harbor-Sleeps 8

Best location in Old Town home, 5 minutes to everything, enjoy the difference!

10.0 out of 10, Exceptional, (3)
"We are long time visitors of Marblehead and this has been one of, if not the best place we’ve stayed so far. The property was well appointed from the kitchen all the way to linens. A great central home that you will love!"
The price is €819
includes taxes & fees
15 Jul - 16 Jul
Best location in Old Town home, 5 minutes to everything, enjoy the difference!

Authentic Rustic Single Family Home in Old Town

10.0 out of 10, Exceptional, (53)
"Natasha was excellent host. The house is perfect. Very cozy, clean and loved how it’s decorated. Close to everything. Adorable. "
The price is €440
includes taxes & fees
13 Jul - 14 Jul
Authentic Rustic Single Family Home in Old Town

Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean

9.8 out of 10, Exceptional, (6)
The price is €781
includes taxes & fees
23 Jul - 24 Jul
Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean

The widow’s walk your very own spa experience

10.0 out of 10, Exceptional, (14)
"Wife and I had a quick stay and loved Marblehead and the surrounding area. House was big but the lair was perfect little a lot for us. "
The price is €598
includes taxes & fees
14 Jul - 15 Jul
The widow’s walk your very own spa experience

Entire Lower Level of the House, Across From The Beach

10.0 out of 10, Exceptional, (15)
"Loved getting to visit the beach and the short drive to Salem!"
The price is €332
includes taxes & fees
20 Jul - 21 Jul
Entire Lower Level of the House, Across From The Beach

Entire 4BR 2 Bath Home l Minutes to Downtown Salem

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great property. Can walk to many things and was a great hub to see beautiful Maine Owner was helpful and quick to respond. "
The price is €551
includes taxes & fees
22 Jul - 23 Jul
Entire 4BR 2 Bath Home l Minutes to Downtown Salem

Beautiful, Cozy Ultra Convenient Salem Home

7.6 out of 10, Good, (39)
"This was a nice little house, which appeared larger in size upon arrival. I enjoyed the comfortable bed and the ability to cook incomparison to a hotel room. "
The price is €324
includes taxes & fees
28 Jul - 29 Jul
Beautiful, Cozy Ultra Convenient Salem Home

Dwtn Beverly! 5 Min to Salem!

The price is €297
includes taxes & fees
4 Aug - 5 Aug
Dwtn Beverly! 5 Min to Salem!

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

9.6 out of 10, Exceptional, (122)
"We stayed here for four days. It’s very clean nice beautiful place."
The price is €277
includes taxes & fees
28 Jul - 29 Jul
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Historic 1686 Home Near Downtown l 5BR Retreat

2.0 star property
9.8 out of 10, Exceptional, (9)
"The house was perfect "
The price is €713
includes taxes & fees
28 Jul - 29 Jul
Historic 1686 Home Near Downtown l 5BR Retreat

NEW 3BR Salem Townhouse Minutes to downtown

10.0 out of 10, Exceptional, (1)
"Perfect size, layout and accommodations for our family! Us and our adult kids! Equipped for lazy nights in with full kitchen and all the amenities of home, comfortable furnishings and clean!! Great porch for relaxing in the mornings and evenings! Perfect location, close enough to walk to all that salem has to offer yet far enough away from the business of it all!"
The price is €712
includes taxes & fees
27 Jul - 28 Jul
NEW 3BR Salem Townhouse Minutes to downtown

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

9.6 out of 10, Exceptional, (80)
"This property is perfect for 2 travelers or for a small family. Close to everything, very clean and easy to get to. Would 100% stay here again!"
The price is €257
includes taxes & fees
23 Jul - 24 Jul
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

*Spooky Halloween 2BR|Downtown+Parking|Hocus Pocus

9.4 out of 10, Exceptional, (41)
"Cute 2 bedroom, I liked the Halloween theme for my daughter. Parking is tight but doable, we had a small suv. Very tiny bathrooms but we made it work. "
The price is €454
includes taxes & fees
20 Jul - 21 Jul
*Spooky Halloween 2BR|Downtown+Parking|Hocus Pocus
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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Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Winter Pond, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its football matches and lake views.

What are some of the best holiday rentals that Winchester has to offer?

Entire Lower Level of the House, Across From The Beach: This holiday home rental outside of Winchester is equipped with a selection of books, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Winchester?

Family-friendly attractions include Winter Pond, whereas Middlesex Fells Reservation is a spot to enjoy the outdoors. TD Garden and Fenway Park are other popular places to visit in the area.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.