Vacation rentals with outdoor seating in Richmond

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Top-rated outdoor seating rentals in Richmond

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Canaan

5.0 out of 5 average rating, 135 reviews

Country Cottage

Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.

Mar 23 – 30

G$32,125 GYD per night

Guest favorite

Home in Lee

4.89 out of 5 average rating, 236 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

Oct 8 – 15

G$25,986 GYD per night

Guest favorite

Guest suite in Richmond

4.92 out of 5 average rating, 170 reviews

Tanglewood/Private Ranch/Kid &Pet Friendly/Horses

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail ride lessons /Horse activities available by appt!

Sep 13 – 20

G$46,187 GYD per night

Guest favorite

Farm stay in New Lebanon

4.95 out of 5 average rating, 185 reviews

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

May 26 – Jun 2

G$48,140 GYD per night

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 185 reviews

Tiny House on 70 Private Acres in Hudson Valley

Welcome to "The Tiny" at The Hemptons in Upstate New York! The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Although we'd encourage you to check out many the local eateries (see below)! The bathroom is full size and likely bigger than the one in your first NYC apartment.

Sep 10 – 17

G$31,956 GYD per night

Guest favorite

Cottage in Kinderhook

4.98 out of 5 average rating, 174 reviews

The Cottage on Sylvester Street

The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.

Sep 27 – Oct 4

G$29,777 GYD per night

Guest favorite

Home in Chatham

4.9 out of 5 average rating, 145 reviews

2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV

WELCOME ALL. Pedestrian/Bike friendly Village home sits 200' to fine dining & Main St pubs/pizza/movies/shopping. 12mi Hudson Amtrak (taxi, Uber avail). Walk to town park w/swim pond. 30mins Albany/Lenox. Keyless entry. Hosts a text away if needed. Smoke/Pet-free property. Check-in 4pm/-out 11a. 55" Sony Roku TV. Reliable high-speed WiFi. Stocked kitchen/full bath incl W/D. Private outdoor dining area w/propane bbq. 2 guests max preferred, a 3rd could be accommodated at extra charge.

Aug 14 – 21

G$24,719 GYD per night

Guest favorite

Guest suite in Hancock

4.83 out of 5 average rating, 155 reviews

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

Mar 23 – 30

G$18,901 GYD per night

Guest favorite

Guesthouse in Lenox

4.95 out of 5 average rating, 284 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Oct 26 – Nov 2

G$30,819 GYD per night

Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 107 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or take a walk on our hiking trail.

Oct 2 – 9

G$26,660 GYD per night

Guest favorite

Apartment in Lenox

4.88 out of 5 average rating, 170 reviews

Station House 1E Private Room & Bath

Our place is a central location in Berkshire County, short drive to restaurants and shops; art and culture, skiing and hiking also close by. You’ll love this former train station( next to the Housatonic RR tracks) which is on three acres between a chapel, the scenic Housatonic River and October Mountain. Our place is good for couples, solo adventurers, and business travelers.

Aug 26 – Sep 2

G$15,275 GYD per night

Guest favorite

Cottage in West Stockbridge

4.98 out of 5 average rating, 108 reviews

Historic 1810 Farmhouse - Fully Renovated

Charm and history meet modern convenience in this stunning renovated farmhouse. Built in 1810, this beautiful home was once the residence of Mr. Prince, who presided over the Tobey Quarry Farm. Just steps into town, the cottage is the ideal retreat for a low-key, cozy getaway. Or as a launch pad to the area's many outdoor/cultural offerings. We warmly welcome you!

May 30 – Jun 6

G$41,610 GYD per night