Chatham Vacation Rentals from SAR 262: Search Short-Term Rentals

Q: What are some of the best vacation home rentals that Chatham has to offer?

Catskill Cottage Walk to Downtown & River Views : This vacation home rental near Chatham offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

A brick building with a green dome and columns, labeled "TRACY MEMORIAL VILLAGE HALL".

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Our top choices for Chatham vacation rentals

A wooden interior with a dining table, chairs, and a window with a view of greenery outside.

1. Sugar Shack - 300 square feet of pure sweetness.

Chatham

Lori S.

SAR 1,185 total

includes taxes & fees

16 Nov - 17 Nov

A modern wooden cabin with a hot tub, wooden deck, and a covered seating area.

2. BLUSH: Boutique TINY homeprivate spawalk to town

Chatham

scott B.

SAR 1,185 total

includes taxes & fees

16 Nov - 17 Nov

A camping setup with a metal chair and a table by a river in a forest.

3. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

Jess S.

SAR 1,227 total

includes taxes & fees

22 Nov - 23 Nov

A modern building with a wooden deck and a door.

4. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Old Chatham

Terri E.

SAR 2,341 total

includes taxes & fees

19 Nov - 20 Nov

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

5. Micosta Leisure Inn

Hudson

George

SAR 347 total

includes taxes & fees

19 Nov - 20 Nov

A large building with a prominent tower, surrounded by trees and a winding road.

6. Berkshire Mountain Lodge

Pittsfield

Susan J

SAR 406 total

includes taxes & fees

6 Dec - 7 Dec

A wooden deck with a staircase leading to a covered porch area.

7. All comforts of home

Hudson

Georgine

SAR 463 total

includes taxes & fees

16 Nov - 17 Nov

8. All the comforts of home

Hudson

Julie B.

SAR 497 total

includes taxes & fees

16 Nov - 17 Nov

9. Vacation Village in the Berkshires

Williamstown

Carol

SAR 378 total

includes taxes & fees

16 Nov - 17 Nov

A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

10. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

Mike

SAR 778 total

includes taxes & fees

14 Dec - 15 Dec

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

11. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Joanna P.

SAR 726 total

includes taxes & fees

16 Nov - 17 Nov

A spacious living room with a dining area, a kitchen, and a large window.

12. 1800s Carriage house in Berkshires / Hudson Valley

New Lebanon

Leslie H.

SAR 795 total

includes taxes & fees

16 Nov - 17 Nov

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

13. Cozy 1-bedroom studio in serene Great Barrington with AC

Great Barrington

bob i.

SAR 434 total

includes taxes & fees

21 Nov - 22 Nov

A backyard with a fire pit, wooden deck, and string lights.

14. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Stottville

Ross O.

SAR 1,307 total

includes taxes & fees

16 Nov - 17 Nov

A bedroom with a wooden bed, a window with a view of trees, and a red chair.

15. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

Sand Lake

Trena

SAR 658 total

includes taxes & fees

16 Nov - 17 Nov

A cabin with a triangular window, wooden walls, and a bed with pillows.

16. Gather Greene

Coxsackie

Jabari

SAR 1,109 total

includes taxes & fees

4 Dec - 5 Dec

A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

17. Hudson NY’S Country Serenity Guest Suite.

Hudson

David P.

SAR 1,362 total

includes taxes & fees

16 Nov - 17 Nov

A wooden cabin with a porch, a door, and a window.

18. Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake

Nathan

SAR 602 total

includes taxes & fees

16 Nov - 17 Nov

A cozy living room with a sofa, a fireplace, and large windows.

19. Luxury Barn Near Hudson With New Private Sauna

East Chatham

Michael T.

SAR 2,350 total

includes taxes & fees

18 Nov - 19 Nov

A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

20. Berkshires Apartment at the Stephentown Hotel

Stephentown

Nicole O.

SAR 789 total

includes taxes & fees

16 Nov - 17 Nov

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Find vacation rentals that suit your style

Top Chatham Hotel Reviews

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Excellent

We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!

Anonymous traveler

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

A lakeside property with a glass conservatory, a pathway leading to a building, and a sunset view.

voco James Newbury Hudson Valley by IHG

Coxsackie

10/10 Excellent

Amy

Two Adirondack chairs facing a river with a forested hill in the background.

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

A residential garden with a pathway leading to a house.

The Amelia

Hudson

10/10 Excellent

Amanda

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

Little Cat Lodge

Copake Falls

10/10 Excellent

Elisabeth

A building entrance with a large planter with purple flowers and a small tree.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

A snow-covered outdoor area with a patio, seating, and a covered dining area.

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

Frequently Asked Questions

Are there vacation rentals in Chatham?

Yes, we have vacation rentals close to top points of interest in Chatham, or you can go with a secluded option if you want a relaxing place to stay. Chatham is known for its theaters and restaurants.

What are some of the best vacation home rentals that Chatham has to offer?

Catskill Cottage Walk to Downtown & River Views: This vacation home rental near Chatham offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Chatham?

With 11 Expedia vacation rentals, you're sure to find just the right place for your Chatham stay.

What can I see and do in Chatham?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Art Omi International Arts Center - Fields Sculpture Park. The Mac-Haydn Theatre and Martin Van Buren National Historic Site are a couple of places you'll find in the larger area.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or more in Chatham. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.

Chatham Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chatham vacation rentals

1. Sugar Shack - 300 square feet of pure sweetness.

2. BLUSH: Boutique TINY home*private spa*walk to town

3. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

4. 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

5. Micosta Leisure Inn

6. Berkshire Mountain Lodge

7. All comforts of home

8. All the comforts of home

9. Vacation Village in the Berkshires

10. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

11. NEW RENO - Chalet-style farm loft near Tanglewood

12. 1800s Carriage house in Berkshires / Hudson Valley

13. Cozy 1-bedroom studio in serene Great Barrington with AC

14. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

15. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway

16. Gather Greene

17. Hudson NY’S Country Serenity Guest Suite.

18. Taborton Harvest Boulder Pines Cabin in the woods

19. Luxury Barn Near Hudson With New Private Sauna

20. Berkshires Apartment at the Stephentown Hotel

Find vacation rentals that suit your style

Top Chatham Hotel Reviews

Inn at Silver Maple Farm

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Chatham?

What are some of the best vacation home rentals that Chatham has to offer?

How many vacation rentals are there in Chatham?

What can I see and do in Chatham?

What are vacation rentals like in Chatham?

2. BLUSH: Boutique TINY homeprivate spawalk to town