Vacation rentals in Andover

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Top-rated vacation rentals in Andover

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Guest favorite

Barn in Andover

4.98 out of 5 average rating, 109 reviews

Fat Cat Barn - Close Okemo & Magic, Vermont

Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

Aug 20 – 27

G$62,230 GYD per night

Guest favorite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond in S Londonderry, VT. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery and hiking right outside your front door. The Cabin has an open floor plan with a galley kitchen, dining/living area with pullout futon couch & 1 full bathroom. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Nov 5 – 12

G$21,367 GYD per night

Guest favorite

Home in Weston

4.86 out of 5 average rating, 106 reviews

4 Bedroom Family Ski House w/ WiFi, cable!

This family heirloom sits tucked away in the trees just off of Chester Mountain Road. Short trips to Bromley, Okemo, Stratton and Magic Mountains. Sleeps 8 comfortably with room for up to 10 on pull out couches. You will fall in love with the retro feel of this house, it's straight out of the 1980's, and has kept that charm over the years. We have consistently updated it with all of the amenities needed to relax, including Air Conditioning, High Speed wifi, Cable, big screen TV and sound bar.

Oct 7 – 14

G$26,392 GYD per night

Guest favorite

Guesthouse in Springfield

4.86 out of 5 average rating, 321 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

Feb 26 – Mar 5

G$19,035 GYD per night

Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 122 reviews

All Season Lovely and Zen Okemo Mt Lodge Condo

Tired of city life and want a fresh breath? Feel the call from nature while also desiring some sporty fun? Come enjoy our lovely and Zen Condo right at the foot of beautiful Okemo! True ski-in/ski-out in the winter. Enjoy your warm ski day lunch by sitting next to the wood-burning fireplace*, while watching all the activities on the slope. In the warm weather, enjoy the beautiful hiking trails and golf course that Okemo offers, as well as water activities at the nearby lakes and rivers.

May 12 – 19

G$19,473 GYD per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 493 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Aug 31 – Sep 7

G$21,418 GYD per night

Guest favorite

Guesthouse in Wallingford

4.98 out of 5 average rating, 588 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

Jan 23 – 30

G$29,788 GYD per night

Guest favorite

Guest suite in Chester

4.91 out of 5 average rating, 155 reviews

Chester Carriage House-Cozy-Quintessential Vermont

Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, yoga studio and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers + breweries. Close proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington) Come experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!

Nov 4 – 11

G$30,503 GYD per night

Guest favorite

Cottage in Windsor

4.97 out of 5 average rating, 318 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins.

Dec 16 – 23

G$28,865 GYD per night

Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 123 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

Aug 26 – Sep 2

G$22,153 GYD per night

Guest favorite

Apartment in Andover

4.98 out of 5 average rating, 386 reviews

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

Sep 16 – 23

G$23,383 GYD per night

Guest favorite

Apartment in Londonderry

4.94 out of 5 average rating, 333 reviews

Cozy Suite in a Historic Building Near Ski Resorts

Located on the second floor of a historical building in the Village of South Londonderry, Vermont, this renovated studio suite features unique touches of modern amenities but with a Vermont feel. Your room will include a 65 inch Smart TV, WiFi, electric fireplace, lush queen bed, full renovated bathroom, small kitchenette, as well as on site parking.

Jun 27 – Jul 4

G$26,891 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Andover vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Andover

Guest favorite

Guest suite in Mt Holly

4.98 out of 5 average rating, 117 reviews

Exquisite Green Mountain Loft Haven

Aug 8 – 15

G$27,400 GYD per night

Guest favorite

Tiny home in Athens

4.95 out of 5 average rating, 148 reviews

Luxury “Tiny” House, Immersed In Nature (Timbery)

Jan 10 – 17

G$52,359 GYD per night

Guest favorite

Home in Weston

4.97 out of 5 average rating, 196 reviews

Weston Farmhouse-Clean, Fast WiFi, Generator!

Sep 7 – 14

G$47,374 GYD per night

Guest favorite

Home in Andover

5.0 out of 5 average rating, 27 reviews

Amazing Views and Sunsets

Jun 14 – 21

G$68,796 GYD per night

Guest favorite

Cabin in Andover

4.95 out of 5 average rating, 55 reviews

Little Cabin on the Ridge

Nov 22 – 29

G$59,958 GYD per night

Guest favorite

Condo in Londonderry

4.95 out of 5 average rating, 43 reviews

Magical Ski-In/Ski-Out Condo at Magic w/ game room

Jul 21 – 28

G$22,274 GYD per night

Guest favorite

Apartment in Weston

5.0 out of 5 average rating, 22 reviews

Peaceful Woods- Suite with Private Entrance

May 10 – 17

G$28,310 GYD per night

Guest favorite

Home in Chester

5.0 out of 5 average rating, 16 reviews

Cozy 1850 farmhouse in Stone Village of Chester

Oct 12 – 19

G$26,145 GYD per night

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Quick stats about vacation rentals in Andover

Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
G$16,679 GYD before taxes and fees

Frequently Asked Questions

Are there pet-friendly vacation rentals in Andover?
Four-legged friends are welcome in Andover. Choose from more than 10 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Andover?
Experience the best of Andover with our house rentals, starting at about $160 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Andover have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Andover. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Andover?
Andover has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Andover have wifi?
Absolutely! We offer over 30 house rentals with wifi in Andover. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Andover?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a kitchen, over 30 homes with wifi, over 10 homes with air conditioning, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Andover have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Andover. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Andover have free parking?
Absolutely! We offer over 20 house rentals with free parking in Andover. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Andover

Top-rated vacation rentals in Andover

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Andover vacation rentals

Other great vacation rentals in Andover

Guest suite in Mt Holly

Tiny home in Athens

Home in Weston

Home in Andover

Cabin in Andover

Condo in Londonderry

Apartment in Weston

Home in Chester

Quick stats about vacation rentals in Andover

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Andover?

How much does it cost to stay in house rentals in Andover?

Do house rentals in Andover have air conditioning?

Are there family-friendly vacation rentals in Andover?

Do house rentals in Andover have wifi?

What are the most popular amenities for House Rentals in Andover?

Do house rentals in Andover have a kitchen?

Do house rentals in Andover have free parking?

Destinations to explore