Holiday rentals in Wakefield

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

Jo-AnnRating, 5 stars7 months ago

This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

4.89 out of 5 average rating, 205 reviews

Apartment in Kennebunk

Over 1000 Five Star Reviews! Walk to Dock Square !

BrandonRating, 5 stars1 week ago

What a wonderful stay my family and I had! With two small children it was so nice to be in walking distance of so much! My wife especially took advantage of the coffee shop next door! Would recommend to family and friends and plan on booking again next year!

4.83 out of 5 average rating, 115 reviews

Home in Conway

A Large Vacation Home with hot tub, game room +

AlecRating, 5 stars2 days ago

Very nice place. Great for a family getaway or a gathering with friends/couples. Most bedrooms have attached bathrooms which was great. Game room was very fun. Fooseball table is broken, so if you’re a rare foose junky like myself don’t plan on it. Only disappointment in this great home. Make sure to bring towels or you’ll be taking a trip to Walmart. Otherwise Highly recommend

4.98 out of 5 average rating, 330 reviews

Flat in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

WarrenRating, 5 stars1 month ago

Hillary's place was a wonderful place to stay for a cozy weekend getaway. It felt very homey with personal touches. We were here during a little snowstorm so we didn't spend any time outside but the yard and private deck were really nice. We had some troubles with the hot water but Hillary was very responsive and helpful! We would definitely stay here again.

4.94 out of 5 average rating, 128 reviews

Home in Windham

Waterfront Gem walkable to Restaurants!

RachaelRating, 5 stars2 days ago

Beautiful house on the pond! Perfect for our family of 4. It was comfortable and relaxing. Amy is a wonderful host! She checked in and made sure we had everything we needed. We really enjoyed our stay! Hoping to stay again sometime.

4.98 out of 5 average rating, 54 reviews

Home in Jackson

The Sommet-Magical Views- Main house+Guest cottage

ChrisRating, 5 stars2 months ago

We loved the views at the Sommet. The house was spacious enough for all 6 of us without even spending much time in the guest house. We found the beds comfortable and the 3 bathrooms were helpful. The kitchen was pretty well stocked and we ended up eating in 5 out of 7 nights. The Uno, Jenga and Clue were big hits with the whole family. Thanks!

4.84 out of 5 average rating, 352 reviews

Home in Conway

Private In Village, HotTub, 1 bedroom, Fire Place

ShelbyRating, 5 stars4 days ago

First time staying at Scott’s NH North Conway home, and it went very well. He and his team were very responsive to any questions I had and the area was a short drive away. The location of the house was a little confusing to find at first but once we realized it was tucked away, the check in process was easy. The house was great for what we needed for the stay. Thanks!

4.92 out of 5 average rating, 167 reviews

Apartment in Lincoln

Cute Resort Studio Apt with Pool, hot tub at Loon

LuciaRating, 5 stars2 weeks ago

Ricky’s place was amazing! Fabulous location just a 10 minute drive from the Franconia Loop Trail (where we hiked). Big studio apartment with a full kitchen & bathroom. Very cute woodsy decor inside & there is a lovely common area in the apartment with board games & and a fire for after dinner activities! We had such a great time!

4.83 out of 5 average rating, 140 reviews

Flat in East End

Fall in LOVE With PORTLAND, MAINE

OliviaRating, 5 stars1 month ago

Stayed for a weekend with 5 people - the space was perfect us! With 3 beds and 2 baths we didn’t feel on top of each other inside. We opted for free street parking which was never an issue. There’s a handful of coffee shops, restaurants and bars with 5-10 min walk. Old Port is about 20 min walk but very easy and safe. We loved being around the block from the ocean and east prom!!

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Popular amenities for Wakefield holiday rentals

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Pool

Free parking on premises

Air conditioning

Stay near Wakefield's top sights

Poor People's Pub33 locals recommend

Tumbledown Café23 locals recommend

Lovell Lake Food Center17 locals recommend

Miss Wakefield Diner & Gracie's Country Store16 locals recommend

Blue Bay Seafood & Steaks14 locals recommend

Knotty Pine Grill & Tavern12 locals recommend

Other great holiday rentals in Wakefield

4.93 out of 5 average rating, 59 reviews

Home in Scarborough

Gorgeous 4 BR home with HOT TUB

ShellyRating, 5 stars1 week ago

Gregory's place was great for our 2 night getaway. Hot tub was amazing and private from neighbors. Bathrooms and kitchens were well stocked. I will definitely go back for another getaway

4.92 out of 5 average rating, 13 reviews

Cabin in Greenwood

All seasons Lake House next to ski areas

GeorgeRating, 5 stars6 months ago

Had a great stay at the cabin. The lake and surrounding mountains are beautiful. Lake was fun to fish off dock and using canoe. Nearby town Bethel has a few nice restaurants and there are a number of easily accessible day hiking spots nearby. The beds are super comfortable as well. Overall a great stay!

4.82 out of 5 average rating, 96 reviews

Home in Tamworth

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim

ShaunaRating, 5 stars2 months ago

The place is clearly well taken care of with attention to detail. This would be a great place any time of year. Miriam and the home were very accommodating. I would return to this location with great peace of mind.

4.97 out of 5 average rating, 63 reviews

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars4 months ago

The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.

5 out of 5 average rating, 49 reviews

Holiday home in Tilton

Cheerful 4 bedroom, lake-front vacation home

JoanRating, 5 stars1 month ago

The house is clean, very easy to access, ample parking space, it actually is more beautiful than how it looks in the photos

4.92 out of 5 average rating, 179 reviews

Cabin in Bartlett

Mountain View Retreat, Near skiing, shopping

JaimeRating, 5 stars3 months ago

We absolutely loved our stay! Plenty of room for 8 guests (and more!!) in a beautiful setting. There was many helpful amenities, like kitchen items, and plenty of towels. The location is perfectly centered to many popular things to do. James was always very responsive to questions left clear instructions. We highly recommend staying here and hope to do so again in the future.

4.85 out of 5 average rating, 105 reviews

Townhouse in Bartlett

Spacious Family Vaca Storyland*Saco*Close to all!

JoanneRating, 5 stars2 months ago

Great place to stay. The basement space for the kids is great, they each had their own bedroom but could hang in the common space. Golden Tee was a HIT! Centrally loacated to multiple ski mountains. Plenty of room to spread out and get comfortable!