20 Best Wolfeboro Vacation rentals on Holiday Lettings - Cottages

Close

Wolfeboro

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

24 Vacation rentals

34

Cottage rental in Wolfeboro with golf nearby

New Hampshire / Wolfeboro

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The Grey Shingles Camps property has been a cottage colony since the 1940's. We have just completed extensive renovations! Our aim is to have our guests experience the vacations of old with a modern sensibility. Rust Pond Camp is the largest of our five camps. We are a …see more

from $225 / night

$1575 / week

Book View

Responds fast!
avg. 2 hours 38 minutes

from $225 / night

(6) Excellent 

100

Cottage rental in Wolfeboro with golf nearby

New Hampshire / Wolfeboro

1 7 Min stay varies

  • 1 bedroom
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose fr …see more

from $129 / night

$903 - $1403 / week

Book View

Responds fast!
avg. 1 hour 6 minutes

from $129 / night

9

Wolfeboro Vacation home rental

New Hampshire / Wolfeboro

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
Comfortable, private family home, walking distance to downtown. Bordered by conservation land with walking trails right off the driveway. Located on private cul-de-sac with no through traffic. Sleeps 9 in 4 bedrooms. Close to all of the amenities of town and Lake Winnip …see more

from $250 / night

$1000 / week

Book View

from $250 / night

(1) Excellent 

34

Vacation home in Wolfeboro

New Hampshire / Wolfeboro

5 18 Min stay varies

  • 5 bedrooms
  • Sleeps 18
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Gorgeous Victorian Main House (newly renovated) that can sleep up to 17 people (open year round) as well as 9 Charming Updated Seasonal Cabin Rentals tucked into the only private woodlands in this “Norman Rockwellesque” Quaint Downtown! Put your keys in a drawer for the …see more

from $199 / night

$1393 / week

Book View

Responds fast!
avg. 1 hour 6 minutes

from $199 / night

14

Wolfeboro Vacation home rental

New Hampshire / Wolfeboro

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Welcome to Nellie's View, an 850 SF lakefront cottage on pristine Rust Pond, in Wolfeboro, New Hampshire! The home is currently being renovated, and will feature a large eat-in kitchen, twin bunk beds, a living room with a cathedral ceiling and queen sofa bed, and a spa …see more

from $240 / night

$1820 / week

Book View

Responds fast!
avg. 2 hours 38 minutes

from $240 / night

(4) Excellent 

32

Vacation cottage in Wolfeboro

New Hampshire / Wolfeboro

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Cute, secluded and modernized lakefront cottage with huge deck and private beach overlooking small lake. 1 double bed, 2 twin beds, 1 queen sofabed. Stunning water views from living room, dining area, kitchen and deck. Small private beach and swimming platform plus use …see more

from $175 / night

$900 - $2310 / week

Book View

from $175 / night

(2) Excellent 

32

Wolfeboro Vacation cottage rental

New Hampshire / Wolfeboro

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The Grey Shingles Camps property has been a cottage colony since the 1940's. We have just completed extensive renovations in our 5 camps and Recreation Hall! Our aim is to have our guests experience the vacations of old with a modern sensibility. In addition to renting …see more

from $205 / night

$1435 / week

Book View

Responds fast!
avg. 2 hours 38 minutes

from $205 / night

(3) Excellent 

91

Cottage rental in Wolfeboro with golf nearby

New Hampshire / Wolfeboro

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose fr …see more

from $99 / night

$693 - $1313 / week

Book View

Responds fast!
avg. 1 hour 6 minutes

from $99 / night

(16) Excellent 

66

Vacation cottage rental

New Hampshire / Wolfeboro

2 9 Min stay varies

  • 2 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose fr …see more

from $169 / night

$1183 - $1533 / week

Book View

Responds fast!
avg. 1 hour 6 minutes

from $169 / night

30

Wolfeboro Vacation cottage rental

New Hampshire / Wolfeboro

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The Grey Shingles Camps property has been a cottage colony since the 1940's. We have just completed extensive renovations! Our aim is to have our guests experience the vacations of old with a modern sensibility! Copple Crown Camp has a view of the great lawn and celebr …see more

from $169 / night

$1183 / week

Book View

Responds fast!
avg. 2 hours 38 minutes

from $169 / night

(3) Excellent 

57

Wolfeboro Vacation home rental

New Hampshire / Wolfeboro

6 15 Min stay varies

  • 6 bedrooms
  • Sleeps 15
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
In Wolfeboro for a wedding, a special event, or just to relax and enjoy all that the Lakes Region has to offer, the Brick House is a spacious home with privacy and room for large families or groups. With six bedrooms, three and a half baths, two screened porches, an ope …see more

from $600 / night

$3500 - $4025 / week

Book View

Responds fast!
avg. 2 hours 15 minutes

from $600 / night

28

Wolfeboro Vacation cottage rental

New Hampshire / Wolfeboro

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The Grey Shingles Camps property has been a cottage colony since the 1940's. We have just competed extensive renovations! Our aim is to have our guests experience the vacations of old with a modern sensibility. Sweet Apple Camp overlooks the Great Lawn, the Ruins, and …see more

from $179 / night

$1363 / week

Book View

Responds fast!
avg. 2 hours 38 minutes

from $179 / night

28

Vacation cottage with golf nearby in Wolfeboro

New Hampshire / Wolfeboro

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
The Grey Shingles Camps property has been a cottage colony since the 1940's. We have just completed extensive renovations! Our aim is to have our guests experience the vacations of old with a modern sensibility! Ehawee Camp overlooks the Great Lawn and has a summer cam …see more

from $169 / night

$1183 / week

Book View

Responds fast!
avg. 2 hours 38 minutes

from $169 / night

37

Vacation cottage with golf nearby in Wolfeboro

New Hampshire / Wolfeboro

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose fr …see more

from $99 / night

$1043 - $1183 / week

Book View

Responds fast!
avg. 1 hour 6 minutes

from $99 / night

39

Vacation home in Wolfeboro

New Hampshire / Wolfeboro

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Bring the dogs to the lakes! Walk to downtown Wolfeboro and the beach. Hop on your bike and coast from the front door to the Bridge Falls Path and pedal as far as you want to go. Bring the kayaks, canoes and stand up paddleboards. Just down the street is the Mast Lan …see more

from $325 / night

$1500 / week

Book View

Responds fast!
avg. 2 hours 15 minutes

from $325 / night

17

Vacation home in Wolfeboro

New Hampshire / Wolfeboro

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Suitable for children age 5+
  • Air conditioning
3-star inn with indoor pool and fitness center Location Situated in Wolfeboro, this inn is within a 15-minute walk of Klickety-Klack Railroad Museum and Wright Museum. Albee Beach and New Hampshire Boat Museum are also within 1 mi (2 km). Property Features An in …see more

from $150 / night

$1050 - $1715 / week

Book View

Responds fast!
avg. 1 hour 24 minutes

from $150 / night

17

Vacation home in Wolfeboro

New Hampshire / Wolfeboro

4 1 night min

  • Sleeps 4
  • 1 night min
  • Suitable for children age 5+
  • Air conditioning
3-star inn with indoor pool and fitness center Location Situated in Wolfeboro, this inn is within a 15-minute walk of Klickety-Klack Railroad Museum and Wright Museum. Albee Beach and New Hampshire Boat Museum are also within 1 mi (2 km). Property Features An in …see more

from $95 / night

$665 - $1260 / week

Book View

Responds fast!
avg. 1 hour 24 minutes

from $95 / night

17

Vacation home in Wolfeboro

New Hampshire / Wolfeboro

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Suitable for children age 5+
  • Air conditioning
3-star inn with indoor pool and fitness center Location Situated in Wolfeboro, this inn is within a 15-minute walk of Klickety-Klack Railroad Museum and Wright Museum. Albee Beach and New Hampshire Boat Museum are also within 1 mi (2 km). Property Features An in …see more

from $115 / night

$805 - $1470 / week

Book View

Responds fast!
avg. 1 hour 24 minutes

from $115 / night

42

Vacation cottage with golf nearby in Wolfeboro

New Hampshire / Wolfeboro

1 7 Min stay varies

  • 1 bedroom
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose fr …see more

from $119 / night

$833 - $1183 / week

Book View

Responds fast!
avg. 1 hour 6 minutes

from $119 / night

43

Vacation cottage with golf nearby in Wolfeboro

New Hampshire / Wolfeboro

1 7 Min stay varies

  • 1 bedroom
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose fr …see more

from $119 / night

$833 - $1523 / week

Book View

Responds fast!
avg. 1 hour 6 minutes

from $119 / night

35

Cottage rental in Wolfeboro with golf nearby

New Hampshire / Wolfeboro

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose fr …see more

from $99 / night

$693 - $1313 / week

Book View

Responds fast!
avg. 1 hour 6 minutes

from $99 / night

8

Vacation home in Wolfeboro

New Hampshire / Wolfeboro

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
A charming 1770 historic farm house! Enjoy "The Ridge" a private 3 bed 2 bath accommodations including linens, towels and a full kitchen with pots/pans and utensils. Plenty of room, home away from home. Enjoy hiking, skiing, swimming, boating, historic sites, museums an …see more

from $171 / night

$1200 - $1815 / week

Book View

from $171 / night

35

Wolfeboro Vacation cottage rental

New Hampshire / Wolfeboro

2 8 Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose fr …see more

from $149 / night

$1043 - $1663 / week

Book View

Responds fast!
avg. 1 hour 6 minutes

from $149 / night

24

Cottage rental in Wolfeboro with golf nearby

New Hampshire / Wolfeboro

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose fr …see more

from $99 / night

$693 - $1383 / week

Book View

Responds fast!
avg. 1 hour 6 minutes

from $99 / night