A lake with autumn-colored trees and a red barn in the foreground.

Rockingham Vacation Rentals

Dates

November 2026

December 2026

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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

Grafton

Kathy H.

AED 1,366 total

includes taxes & fees

9 Nov - 10 Nov

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

Ludlow

Vanessa W.

AED 942 total

includes taxes & fees

9 Nov - 10 Nov

3. Charming Chester Farmhouse near Near VT Slopes

Chester Depot

Kimberly B.

AED 1,386 total

includes taxes & fees

9 Nov - 10 Nov

A view through a window with a wooden frame, revealing a forested area with snow on the ground.

4. Cozy cabin in charming Londonderry

Londonderry

Eric H.

AED 961 total

includes taxes & fees

9 Nov - 10 Nov

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

Ludlow

AED 1,058 total

includes taxes & fees

11 Nov - 12 Nov

A wooden deck with a white railing overlooking a lake, surrounded by trees and a small house.

6. Lakefront Family Fun Retreat

Newport

sean c.

AED 1,485 total

includes taxes & fees

10 Nov - 11 Nov

A two-story house with a deck, surrounded by dense forest.

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

Chester

pauline

AED 3,518 total

includes taxes & fees

9 Nov - 10 Nov

A garden with a wooden pergola, purple flowers, and a river view.

8. Family Friendly Hilltop House In Putney Vermont

Putney

Susan G.

AED 971 total

includes taxes & fees

9 Nov - 10 Nov

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

Clock Tower Base Area

tiliger01

AED 837 total

includes taxes & fees

11 Nov - 12 Nov

Nature, fresh air, and peaceful pond views

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

Ludlow

AED 1,606 total

includes taxes & fees

9 Nov - 10 Nov

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

Stratton

AED 934 total

includes taxes & fees

9 Nov - 10 Nov

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

Clock Tower Base Area

Danna K.

AED 967 total

includes taxes & fees

11 Nov - 12 Nov

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

Andover

Lorraine C.

AED 2,464 total

includes taxes & fees

9 Nov - 10 Nov

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!

Newfane

Joseph P.

AED 1,020 total

includes taxes & fees

16 Nov - 17 Nov

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

Ludlow

Brian

AED 1,122 total

includes taxes & fees

11 Nov - 12 Nov

A paved courtyard with a bench, a white fence, and buildings with balconies.

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

Stratton

AED 826 total

includes taxes & fees

9 Nov - 10 Nov

A wooden cabin with a balcony and a staircase leading to a second level.

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

londonderry

Tracey V.

AED 2,267 total

includes taxes & fees

16 Nov - 17 Nov

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

Ludlow

Zach S.

AED 1,004 total

includes taxes & fees

11 Nov - 12 Nov

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

Londonderry

Michael D.

AED 1,280 total

includes taxes & fees

16 Nov - 17 Nov

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

Ludlow

Frank R.

AED 864 total

includes taxes & fees

11 Nov - 12 Nov

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Find vacation rentals that suit your style

Top Rockingham Hotel Reviews

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

Harvest Barn Inn

Bellows Falls

10/10 Excellent

Virginia

A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

Best Western Springfield Hotel

Springfield

10/10 Excellent

JULIA

A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.

The Common Man Inn & Restaurant

Claremont

10/10 Excellent

Robert

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

Stone Hearth Inn and Eatery

Chester

10/10 Excellent

William

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

Four Columns Inn

Newfane

10/10 Excellent

Nettie

A cozy living room with a stone fireplace, a leather sofa set, a wooden coffee table, and a patterned rug.

Fullerton Inn

Chester Depot

10/10 Excellent

Catherine

A modern outdoor lounge area with two lounge chairs and a wooden deck.

Otherland Hotel

Newfane

10/10 Excellent

The property is very well maintained and decorated. The room and bathroom are very clean. It has two very nice common area with 2 big windows that made them bright and sunny and cozy. It's also along a major highway so it's easy to find. The owners/operators of this hotel are very kind, thoughtful and accomodating to the needs of their guests. I especially and directly experienced their wonderful hospitality as a disabled person in a wheelchair. When I inquired about the accessibility of...

Rosalie

A dock extending into a lake with a grassy area in the foreground and trees in the background.

Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

10/10 Excellent

James

A stone fire pit with flames in front of a house with a covered porch and blue lighting.

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

10/10 Excellent

Anthony

A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.

Blue Gentian Lodge at Magic Mountain

Londonderry

10/10 Excellent

Anonymous traveler

A dining area with wooden tables and chairs, large windows with a view of trees, and a bench along the wall.

The Carriage Barn Inn

Keene

10/10 Excellent

Richard

A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

Main and Mountain Bar & Motel

Ludlow

10/10 Excellent

Anonymous traveler

A modern dining area with a central seating area, a kitchen in the background, and large windows providing natural light.

Hampton Inn & Suites Keene

Keene

10/10 Excellent

kristin

A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

Pointe at Castle Hill Resort

Cavendish

10/10 Excellent

This is the second time we've stayed in a Suite room. King sized bed in the BR; kitchen with full-sized appliances, LR with pull-out Queen sofa, gas fireplace, bathroom with jetted tub! Very comfortable and fully equipped. Small things were so helpful - like doormats for dirty boots, a bench for putting on boots, a closet for skis, complementary packages of New England coffee, Aveda products in the bathroom, kitchen supplies like dish soap, dishwasher detergent, sponge, towels. Then larger...

Marion

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.

Rockingham Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Rockingham vacation rentals

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

2. Cozy Village Condo-Okemo Shuttle

3. Charming Chester Farmhouse near Near VT Slopes

4. Cozy cabin in charming Londonderry

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

6. Lakefront Family Fun Retreat

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

8. Family Friendly Hilltop House In Putney Vermont

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

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

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

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

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

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

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

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

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

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

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

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

Find vacation rentals that suit your style

Top Rockingham Hotel Reviews

Harvest Barn Inn

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Rockingham?

What are some of the best vacation rentals in Rockingham?

How many vacation rentals are there in Rockingham?

What can I see and do in Rockingham?

What are vacation rentals like in Rockingham?