Holiday Rentals in Brewster

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Check prices for these dates

Holiday Rentals in Brewster

The Hideaway

10.0 out of 10, Exceptional, (4)
"Me and my family stayed here for a quick get-away out of the city. Very pretty location, and loved our stay here! Thanks!"
The price is €259
includes taxes & fees
13 Mar - 14 Mar
The Hideaway

Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

8.8 out of 10, Excellent, (5)
"Truly a gem of a place! We loved it. Great spot to celebrate my 30th birthday with a low-key, mellow group. My chef friend who cooked the entire weekend was thrilled at the industrial-style kitchen. The house is probably unlike anything you've ever seen. We're still talking about it haha. A lovely spot. "
The price is €1,226
includes taxes & fees
21 Mar - 22 Mar
Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

10.0 out of 10, Exceptional, (2)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is €278
includes taxes & fees
19 Mar - 20 Mar
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (108)
"Awesome "
The price is €227
includes taxes & fees
13 Mar - 14 Mar
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (38)
"We were a family of 4 adults and 2 toddlers staying over Thanksgiving. We really didn’t need all the space but we certainly enjoyed it. There’s a huge well stocked kitchen, kids’ play areas on both the main floor and basement, and the property is massive and gorgeous. Great stay!"
Over Sized Colonial on Private Road.

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

10.0 out of 10, Exceptional, (106)
"The title says it all really. The house is as well equipped as your home, superbly comfortable, has glorious views East over the lake, has space for everyone and was just a delight to stay in. Lisa is so repsonsive, thoughtful and kind, which just adds to the warmth of feeling and quality of experience. Thank you very much indeed. "
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

9.2 out of 10, Wonderful, (33)
"Perfect spot for a get together with friends... kitchen, dining room and living room all connected so you're always together and not missing out on the fun. Comfy couches and plenty of space for large board games."
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

9.4 out of 10, Exceptional, (9)
"We stayed here for work event and the location was perfect. Not too close, not too far away. Its snowed one evening but the driveway was not slippery at all. The house was very clean and kept in order. Plenty of room in the bedrooms and bathroom. The operational fireplace was also an added bonus. "
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (95)
"House is absolutely perfect! This is our second time staying and we will definitely return. So much charm and warmth. I had the best sleep that I have had in months. All the amenities you could ask for, and more. Terrific convenient location. Host goes above and beyond to make sure we are comfortable. "
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

9.4 out of 10, Exceptional, (87)
"The parking situation was a bit tricky because there was no good way to back in. Other than that, location was great - cute area! "
Lake Cottage, Kayaks, FirePit, Grill & Deck, 1 hour & 15 Minutes to NYC!

Chestnut - Charming 3-bedroom cottage in wonderful Fishkill!

Chestnut - Charming 3-bedroom cottage in wonderful Fishkill!

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (76)
"The house was super clean and very easy to take care of while we were here. It was perfect for a remote getaway, hiking and just being quiet. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (16)
"It was a quick trip to see woman’s army basketball game. It was an excellent stay and excellent accommodations. "
The price is €353
includes taxes & fees
17 Mar - 18 Mar
Contemporary Cozy Cottage

Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

9.6 out of 10, Exceptional, (84)
"My girlfriends and mine were looking for a nice weekend getaway to unwind. The property was very clean. The basement level seemed a little more disheveled than pictured and very cold. Unfortunately we didn’t spend any time down there. The rest of the property was wonderful and spotless! Beds were comfortable."
Lakehouse; Kayaks, Grill, FirePit, Gym, Movie Room, Pool Table, Air Hockey etc!

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (18)
"We had a friend group boardgaming weekend and this was perfect for our purposes. The table was large enough for our biggest games and the pool table doubled as a backup playing space. The race cars are a nice touch of whimsy too :-) Our only suggestion would be to replace the oversized, too-low chandelier over the table but really only a minor thing."
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (40)
"Considering that area does not have convenient hotels, this location was perfect for the event we attended. It was nice of them to vacate their home so we could stay - though we wish that would have been communicated. There is no extra room with twin beds - at least not functional. The property is nice. Whomever took the pictures did a great job. It worked for us for the short time we were in the area."
Litchfield County Four Season Country Paradise

Westport Retreat - Private Stay, Walk to Main Street, Office Space, Patio, Garage, & High-Speed WiFi

Westport Retreat - Private Stay, Walk to Main Street, Office Space, Patio, Garage, & High-Speed WiFi

Pet-Friendly Beacon Area Vacation Rental: 6 Acres

10.0 out of 10, Exceptional, (12)
"Great place to stay for all ages. Had everything we needed and lots of room to relax. Definitely will stay here again next time we come. Comfy beds, easy to get to, easy check in, everything we needed in the kitchen, lots of books and toys, great outdoor space. Thanks for providing the perfect place to stay with extended family! "
Pet-Friendly Beacon Area Vacation Rental: 6 Acres

Charming 3-bedroom house with AC, WiFi in Peekskill

Charming 3-bedroom house with AC, WiFi in Peekskill

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (28)
"Our family's stay at Helen and Richie's property for the holidays was perfect. Waking up to views of the lake every morning, watching flocks of birds travel on the water and being surrounded by nature was all we could ask for. The house has all amenities provided in the kitchen, bathrooms etc. Location is convenient near shops, grocery, and restaurants in New Fairfield. The hosts were very responsive in communication and I appreciated them providing everything we needed. "
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
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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Other types of properties in Brewster you may be interested in

Heidi's Inn

2.5 star property
8.8 out of 10, Excellent, (698)
"Great place to stay "
The price is €115
includes taxes & fees
17 Mar - 18 Mar
Heidi's Inn

Comfort Inn

2.5 star property
9.0 out of 10, Wonderful, (407)
"The front desk gentleman was very kind and helpful. It was a good night stay all together."
The price is €134
includes taxes & fees
16 Mar - 17 Mar
Comfort Inn

The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.

9.8 out of 10, Exceptional, (9)
"Our stay at the cottage was really great, Orestes is an amazing host. The cottage was cozy, clean, and quiet and very dog friendly. Highly recommended!"
The Cottage by the Lake: Hudson Valley Indulgence/1 hr. from NYC/welcome pets!.
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.

Frequently asked questions

Can I find a holiday rental in Brewster?

Yes, there are holiday rentals close to the most popular sights in Brewster, or you can select a more secluded option if you're looking for a relaxing stay. Brewster is known for its shopping and restaurants. Make sure you have time to check out the entertainment choices and live music during your trip.

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Brewster offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include an oven, a microwave and kitchenware. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Brewster?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Brewster stay.

What’s there to see and do in Brewster?

Explore the area and cultural attractions such as Kouros Sculpture Center, or visit one of the family-friendly sights such as SplashDown Beach. Brewster Public Library and Centennial Golf Club are a couple of places you'll find in the wider area.

What’s a holiday rental in Brewster like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Brewster. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.