Charlestown Vacation Rentals from $243: Search Short-Term Rentals

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

Family Friendly Hilltop House In Putney Vermont : This vacation home rental near Charlestown is located on a lake and has a balcony, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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In two weeks

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Our top choices for Charlestown vacation rentals

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

Grafton

Eleanor D.

$330 nightly

Aug 31 - Sep 1

Total with taxes and fees

2. Explore the upper valley from this spacious Claremont Home

Claremont

$343 nightly

Aug 31 - Sep 1

Total with taxes and fees

3. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

Chester

pauline

$901 nightly

Sep 6 - Sep 7

Total with taxes and fees

4. Charming Chester Farmhouse near Near VT Slopes

Chester Depot

Kimberly B.

$382 nightly

Sep 1 - Sep 2

Total with taxes and fees

5. Lakefront Family Fun Retreat

Newport

Ann R.

$383 nightly

Sep 1 - Sep 2

Total with taxes and fees

6. Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cavendish

John H.

$332 nightly

Aug 31 - Sep 1

Total with taxes and fees

7. Terrific 3-bedroom cottage with AC in charming Cavendish

Cavendish

Mark G.

$539 nightly

Aug 31 - Sep 1

Total with taxes and fees

8. Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Walpole

mary c.

$640 nightly

Sep 3 - Sep 4

Total with taxes and fees

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Top Charlestown Hotel Reviews

Days Inn by Wyndham Keene NH

8/10 Good

"The staff was helpful. Parking was easy. It was an ok stay. I would stay there again for the price."

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

8/10 Good

"First, the service was amazing. The afternoon/evening front desk gentlemen was extremely kind and helpful as we navigated an issue with the room we were originally given (that turned out to not be an issue so won’t bother mentioning). The rooms were slightly dated but clean and well maintained. The only downside of the room was the carpet - it wasn’t awful but was old and a bit musty. We are very sensitive to smells and allergens so others may not notice. That said it didn’t affect our allergies too much so it wasn’t that bad. Room comes with basic cooking equipment, plates and silverware. The room we got was a two bedroom but the queen bedroom doesn’t have a door that closes - it’s a separate room but is open to the living room/kitchen. This wasn’t an issue for us but worth noting for others. Beds were clean and looked new but weren’t the nicest mattresses. Same with the pillows. We did go to the indoor pools - it was pretty well maintained. They had locker rooms and a dry sauna but we didn’t use either. Continental breakfast was as you’d expect. Nothing hot was served but lots of options - including a whole gluten free section which you NEVER see at hotels and I great appreciated. The hotel was nice and the staff great but it definitely had “we were a reeeallly nice hotel before the pandemic and then we lost a lot of our extras” vibes. They used to have a spa, a bar, an outdoor pool and a restaurant but those are all gone. It was fine as is though."

Find out more about Charlestown

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

Charlestown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Charlestown. 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 Charlestown 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 $243 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 Charlestown rentals

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

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Things to do in Charlestown

Frequently asked questions

Can I find a vacation rental in Charlestown?

Yes, we offer vacation rentals close to the most popular sights in Charlestown, or you can go with a more remote option if you want a relaxing place to stay. Charlestown is known for its university setting and museums.

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

Family Friendly Hilltop House In Putney Vermont: This vacation home rental near Charlestown is located on a lake and has a balcony, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Charlestown?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Charlestown stay.

What’s there to see and do in Charlestown?

Connecticut River State Park and Connecticut River are a couple of scenic spots to enjoy the outdoors, whereas The Fort at No.4 Open Air Museum is one of the cultural attractions. Charlestown Town Hall and Silsby Free Public Library are other places to visit while you're in town.

What’s a vacation rental in Charlestown like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Charlestown. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.

Room 1

Check prices for these dates

Our top choices for Charlestown vacation rentals

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

2. Explore the upper valley from this spacious Claremont Home

3. 4-Season Vermont Cabin · 12 Acres, Mountain Views · Okemo

4. Charming Chester Farmhouse near Near VT Slopes

5. Lakefront Family Fun Retreat

6. Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

7. Terrific 3-bedroom cottage with AC in charming Cavendish

8. Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

9. Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

10. Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls

11. Brook Road Cabin

12. Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

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

14. Fat Sheep Farm & Cabins

15. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

16. New Ludlow Village Home with Stunning Okemo Mountain View

17. Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

18. @SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee

19. Large Farmhouse with expansive views, firepit 15 min north of Keene

20. The Treehouse at 11 Gables Ludlow – Dining, Shopping & Okemo Shuttle

Find vacation rentals that suit your style

Top Charlestown Hotel Reviews

Days Inn by Wyndham Keene NH

Keene Elm City Hotel, an Ascend Collection Hotel

Mountain Edge Suites at Sunapee, an Ascend Collection Hotel

The Common Man Inn & Restaurant

The Putney Inn

Best Western Plus Keene Hotel

Courtyard by Marriott Keene Downtown

Fairfield Inn & Suites by Marriott Keene Downtown

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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