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Rockingham Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Rockingham vacation rentals

A red house with a covered porch and a chimney.

1. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (175 reviews)
"Very pet friendly & nice country location. Host was responsive & helpful."
United States
Neil S.
$323 nightly
The price is $362
Nov 9 - Nov 10
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A modern kitchen with stainless steel appliances, a wooden dining table set for four, and a seating area with a sofa and chairs.

2. Cozy Village Condo-Okemo Shuttle

Cozy Village Condo-Okemo Shuttle
Ludlow
9.8 out of 10, Exceptional, (89 reviews)
"Great place to stay, very easy to get to. A cozy and comfortable place, that is always clean. There are postings and labels throughout, which is very helpful. Hosts are great and make the experience very easy. Oh and the bed is amazing!!"
United States
Vanessa W.
$221 nightly
The price is $250
Nov 9 - Nov 10
Total with taxes and fees
Cozy Village Condo-Okemo Shuttle
Dining

3. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful classic farmhouse in lovely neighbourhood."
United States
Kimberly B.
$328 nightly
The price is $367
Nov 9 - Nov 10
Total with taxes and fees
Charming Chester Farmhouse near Near VT Slopes
A view through a window with a wooden frame, revealing a forested area with snow on the ground.

4. Cozy cabin in charming Londonderry

Cozy cabin in charming Londonderry
Londonderry
8.4 out of 10, Very good, (5 reviews)
"Very cozy and quiet. "
United States
Eric H.
$225 nightly
The price is $254
Nov 9 - Nov 10
Total with taxes and fees
Cozy cabin in charming Londonderry
A cozy cabin interior with a sofa, dining table, chairs, wooden cabinets, and a kitchen area.

5. Condo a short walk to the Sachem trail with seasonal pool and tennis

Condo a short walk to the Sachem trail with seasonal pool and tennis
Ludlow
$255 nightly
The price is $288
Nov 11 - Nov 12
Total with taxes and fees
Condo a short walk to the Sachem trail with seasonal pool and tennis
A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

6. Lakefront Family Fun Retreat

Lakefront Family Fun Retreat
Newport
10.0 out of 10, Exceptional, (5 reviews)
"Had a lot here to use and The place was very cute. It’s good if you have small kids they have a lot for that sort of thing. Very clean as well"
United States
sean c.
$363 nightly
The price is $393
Nov 10 - Nov 11
Total with taxes and fees
Lakefront Family Fun Retreat
A two-story house with a deck, surrounded by dense forest.

7. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
Chester
10.0 out of 10, Exceptional, (6 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
$831 nightly
The price is $931
Nov 9 - Nov 10
Total with taxes and fees
4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo
A garden with a wooden pergola, purple flowers, and a river view.

8. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (65 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
$230 nightly
The price is $258
Nov 9 - Nov 10
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
A living room with a sofa, a bench, a fireplace, a TV, and a large window.

9. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge

Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
$202 nightly
The price is $228
Nov 11 - Nov 12
Total with taxes and fees
Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
A room with a stone fireplace, wooden ceiling, and a window with curtains.

10. Peaceful Stay w/ Pond & Massage Chair | Near Okemo

Peaceful Stay w/ Pond & Massage Chair | Near Okemo
Ludlow
$386 nightly
The price is $425
Nov 9 - Nov 10
Total with taxes and fees
Peaceful Stay w/ Pond & Massage Chair | Near Okemo
A spacious living room with a fireplace, leather sofas, a Christmas tree, and large windows.

11. Long Trail House 368 condo in Stratton Village, walk to the lifts

Long Trail House 368 condo in Stratton Village, walk to the lifts
Stratton
$225 nightly
The price is $254
Nov 9 - Nov 10
Total with taxes and fees
Long Trail House 368 condo in Stratton Village, walk to the lifts
A building with multiple floors, a red curved structure, and a flower bed with purple flowers.

12. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts

Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
Clock Tower Base Area
8.8 out of 10, Excellent, (81 reviews)
"It was a perfect location and had everything we needed for a great stay."
United States
Danna K.
$233 nightly
The price is $263
Nov 11 - Nov 12
Total with taxes and fees
Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
A cozy living room with a stone fireplace, large windows, and a wooden ceiling.

13. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
10.0 out of 10, Exceptional, (2 reviews)
"Very nice stay. Owners were very gracious. House was clean & comfortable."
United States
Lorraine C.
$582 nightly
The price is $652
Nov 9 - Nov 10
Total with taxes and fees
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

14. Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
$241 nightly
The price is $270
Nov 16 - Nov 17
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
A two-story house with a porch, a staircase, and a front door.

15. First-floor downtown studio near dining and gear shops, under a mile to Okemo

First-floor downtown studio near dining and gear shops, under a mile to Okemo
Ludlow
8.8 out of 10, Excellent, (14 reviews)
"This place was so close to Okemo, and walking distance to the local pub and restaurants."
United States
Brian
$270 nightly
The price is $305
Nov 11 - Nov 12
Total with taxes and fees
First-floor downtown studio near dining and gear shops, under a mile to Okemo
A building with a sign reading 'Landmark' and a large spherical sculpture in the center.

16. Fourth-floor Stratton Village studio with valley-view balcony

Fourth-floor Stratton Village studio with valley-view balcony
Stratton
$199 nightly
The price is $225
Nov 9 - Nov 10
Total with taxes and fees
Fourth-floor Stratton Village studio with valley-view balcony
A wooden cabin with a balcony and a staircase leading to a second level.

17. Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
9.0 out of 10, Wonderful, (7 reviews)
"Beautiful location and place. Could have been a bit cleaner (windows, TV, shower curtain) and the hot tub worked well but definitely needed to be cleaner."
United States
Tracey V.
$531 nightly
The price is $600
Nov 9 - Nov 10
Total with taxes and fees
Romantic Riverbed Treehouse - hot tub & new sauna!
A two-story house with a porch, a staircase, and a front door.

18. Downtown Ludlow condo with electric fireplace, shuttle stop across the street

Downtown Ludlow condo with electric fireplace, shuttle stop across the street
Ludlow
8.8 out of 10, Excellent, (27 reviews)
"Easy stay. Great location."
United States
Zach S.
$242 nightly
The price is $273
Nov 11 - Nov 12
Total with taxes and fees
Downtown Ludlow condo with electric fireplace, shuttle stop across the street
A cozy cabin interior with a wooden ceiling, a round table with chairs, a fireplace, and a large window overlooking a snowy landscape.

19. Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
Londonderry
10.0 out of 10, Exceptional, (3 reviews)
"Stay is very cozy and rustic. Be prepared for house to be cold when you show up. Host is very responsive and accommodating."
United States
Michael D.
$300 nightly
The price is $338
Nov 9 - Nov 10
Total with taxes and fees
Beautiful country cabin with hot tub and outdoor shower in Londonderry
A two-story house with a covered porch, a staircase, and a front door with a wreath.

20. Compact downtown studio condo with kitchenette near the Okemo slopes

Compact downtown studio condo with kitchenette near the Okemo slopes
Ludlow
8.6 out of 10, Excellent, (34 reviews)
"the home was clean and very nice. "
United States
Frank R.
$208 nightly
The price is $235
Nov 11 - Nov 12
Total with taxes and fees
Compact downtown studio condo with kitchenette near the Okemo slopes
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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Top Rockingham Hotel Reviews

Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"A perfectly okay place to stay; convenient location, fairly comfortable bed, good shower!"
Rob 2-night trip
Posted less than an hour ago
Hampton Inn Brattleboro

Find out more about Rockingham

Everything you need to know about Rockingham 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 Rockingham 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 Rockingham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Rockingham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Rockingham. 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 Rockingham 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 $362 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 Rockingham rentals

At Expedia, we put the best Rockingham 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 Rockingham 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 Rockingham 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 Rockingham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Rockingham?

Yes, there are vacation rentals in Rockingham close to Vermont Country Store, or you can select a secluded option if you'd like a relaxing place to stay. Rockingham is known for its coffeehouses and waterfalls. Make sure you have time to check out the ski areas and festivals during your trip.

What are some of the best vacation rentals in Rockingham?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home rental near Rockingham is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Rockingham?

Expedia has 3 vacation rentals for your stay in Rockingham.

What can I see and do in Rockingham?

Connecticut River and Saxtons River Recreation Area are a couple of scenic spots to enjoy the outdoors, whereas Bellows Falls Opera House is one of the cultural attractions. Other places in town to visit include Vermont Country Store and Bellows Falls Fish Ladder.

What are vacation rentals like in Rockingham?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Rockingham. Vacation rentals feature extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for families.