Raymond vacation rentals

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Top-rated vacation rentals in Raymond

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Guest favorite

Guest suite in Bridgton

4.98 out of 5 average rating, 165 reviews

Barn on Pleasant-walk to town

Welcome to our charming loft in a peaceful neighborhood, ideal for comfort and convenience. This well maintained property provides a cozy living space. The loft features a kitchenette, a beautiful stone fireplace and a big, comfy reclining couch. Visit Bridgton this spring and summer, walking distance to Highland Lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring

Nov 22 – 29

R2,947 ZAR per night

Guest favorite

Guest suite in New Gloucester

4.98 out of 5 average rating, 172 reviews

Peaceful Lakeside Suite w/Firepit and Kayaks

Open the double doors of your suite for direct access to a beautiful Maine lake. With a private entrance, the open concept apartment is in the walk-out basement of our log-cabin style home. Includes a kitchenette, private bathroom, enclosed unheated porch, large flat screen TV with DirecTV, washer & dryer. A patio with firepit is available (except when snow-covered). You may swim and use our kayaks and other boats, in season, at your own risk. Nice views. Quiet and peaceful. Enjoy star-gazing.

May 4 – 9

R2,172 ZAR per night

Guest favorite

Guest suite in Raymond, Maine

4.91 out of 5 average rating, 122 reviews

Rustic knotty pine getaway

lovely completely newly remodeled 2 bedroom 1-1/2 bath completely private upstairs unit with kitchen and private screened in deck. It has a private entrance with plenty of off street parking. located in Maine's lake region area. Walking distance to Raymond beach on Sebago lake. 5 miles to restaurants, shopping and local entertainment. 15 Miles from Portland. 30 to 60 minutes to winter skiing. Kayak, boat, and jet ski rentals nearby. 30 minutes to casino. Electric Vehicle charging on site.

Oct 16 – 23

R5,063 ZAR per night

Guest favorite

Loft in Bridgton

4.95 out of 5 average rating, 551 reviews

Tap House Loft~Sunny & Spacious, Private Hot Tub

Conveniently located in the heart of Downtown Bridgton, the Tap House Loft is ready for you, your friends and your family to enjoy! Walk to vibrant Main Street, Pondicherry Park, the Magic Lantern Theater, Highland Lake and all the downtown shops, gallerias and restaurants...or simply relax in the peace and quiet of our newly restored, historic warehouse. Located above the Sundown Lounge, this 900 sq ft space offers a large Master Suite with French Doors leading to a deck and hot tub.

Nov 1 – 8

R3,294 ZAR per night

Guest favorite

Cabin in Raymond

4.93 out of 5 average rating, 144 reviews

Rustic, cozy cabin on Sebago Lake. A hidden gem.

Step out of the screened in patio to lakeside relaxation. Dive into crystal waters, snorkel or float with a cool beverage. Kayak or canoe out to Turtle Cove and enjoy the wildlife in this natural waterway teeming with birds to include our resident Blue Heron, ducks, geese, and loons who make this place their home. We have the fortune of bald eagle pairs in several tall pines. Turtles sunning on doting rocks and lily pads in bloom greet us each day. It is a natural water landscape.

Sep 19 – 26

R3,513 ZAR per night

Guest favorite

Farm stay in Gray

4.88 out of 5 average rating, 241 reviews

The Retreat at Crystal Lake Farm

This getaway features two spacious bedrooms plus an upstairs bedroom loft, sleeping up to 6 with ease. The large bathroom is accessed by both the master bedroom and living room and features on-site laundry. For guests who love to cook the kitchen is fully equipped and the deck is a perfect place to relax in the summer and enjoy the view. In colder seasons guests are encouraged to cozy up by the wood-burning stove or use the outdoor BARREL SAUNA.

Jul 9 – 16

R3,379 ZAR per night

Guest favorite

Cabin in Naples

4.87 out of 5 average rating, 115 reviews

Songo Lock Cabins #1

Cabins on the waterSongo Lock Cabins are located at the Historical Songo Locks. The cabins are over 100 years old and date back to the early 1900's.. Every year we add new things . The cabins are on the water and have their own dock. The Songo Locks is hand operated and opens to allow boats in and lowers them so they can continue down river into Sebago Lake. You can sit at your cabin and watch the boats or grab a fish pole and do some fishing.

Jun 17 – 24

R2,622 ZAR per night

Guest favorite

Guesthouse in Windham

5.0 out of 5 average rating, 218 reviews

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

May 23 – 30

R2,421 ZAR per night

Guest favorite

Guest suite in Windham

4.92 out of 5 average rating, 151 reviews

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 100(mbps) for a work from home atmosphere.

Nov 2 – 9

R2,203 ZAR per night

Guest favorite

Cabin in Lovell

4.98 out of 5 average rating, 253 reviews

Secluded, cozy cabin nestled in the Maine woods

Kick back and relax in this calm, stylish space with a semi-remote cabin experience while keeping the gentle daily living comforts. Right at the edge of the White Mountain National Forest in one direction and in the other direction, a short five minute drive to Kezar Lake this secluded cabin has it all for the nature lover in you! Close to local favorite trailheads for hiking and mountain biking.

Dec 23 – 30

R2,175 ZAR per night

Guest favorite

Cabin in Raymond

4.96 out of 5 average rating, 164 reviews

Idyllic Lakeside Cabin

Situated on a beautiful lake with 350 feet of private shoreline the cabin is ideal for family gatherings or a small group of friends, it is not available for parties and events. A seven day minimum stay is required for summer months. Cozy up with board games, a book and enjoy the tranquility. We have firewood on the property for you to use. The docks are not in the water from October to April.

Dec 6 – 13

R8,885 ZAR per night

Guest favorite

Farm stay in Gray

4.94 out of 5 average rating, 246 reviews

Great Goat Get-away in Southern Maine!

This quiet and cozy house is located in the woods at the renowned Ten Apple Farm. Centrally located in Southern ME, we're just a short drive from Portland, lakes, ski areas, LL Bean and more! On the farm you can meet and interact with our herd of goats, sheep, pigs and chickens, learn to milk, collect eggs, and arrange on of our famous goat hikes!

Feb 18 – 25

R2,743 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Raymond vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Raymond's top sights

Seacoast Adventure59 locals recommend

Walmart Supercenter14 locals recommend

Point Sebago6 locals recommend

Bob's Seafood43 locals recommend

Pat's Pizza23 locals recommend

Applebee's Grill + Bar4 locals recommend

Other great vacation rentals in Raymond

Guest favorite

Guest suite in Lewiston

4.97 out of 5 average rating, 191 reviews

Sanctuary in the City

Oct 28 – Nov 4

R2,611 ZAR per night

Guest favorite

Apartment in Casco

4.9 out of 5 average rating, 30 reviews

Country Village Getaway

Mar 15 – 22

R2,183 ZAR per night

Guest favorite

Cottage in Raymond

4.95 out of 5 average rating, 22 reviews

Relaxing New England Lakeside Getaway

Aug 21 – 28

R6,476 ZAR per night

Guest favorite

Cottage in Raymond

4.9 out of 5 average rating, 90 reviews

Relax by a Quiet Lake

Oct 10 – 17

R3,196 ZAR per night

Guest favorite

Home in Raymond

5.0 out of 5 average rating, 29 reviews

Cheerful 3 Bedroom Home for your Maine Getaway

May 29 – Jun 5

R4,323 ZAR per night

Guest favorite

Apartment in Gray

4.96 out of 5 average rating, 26 reviews

A lovely 2 Bedroom Apt 1st FL w/ backyard and deck

Apr 24 – May 1

R2,186 ZAR per night

Superhost

Cottage in Windham

4.9 out of 5 average rating, 10 reviews

Relaxing 2 bed cottage on Little Sebago Lake

May 28 – Jun 4

R5,766 ZAR per night

Guest favorite

Cottage in Raymond

4.89 out of 5 average rating, 19 reviews

Hawthorne Cottages Lakeside

Jun 10 – 17

R3,688 ZAR per night

Show all

Other great vacation rentals in Raymond

Guest favorite

Home in Raymond

4.94 out of 5 average rating, 49 reviews

Lakehouse Retreat on Jordan Bay, Sebago Lake

Nov 5 – 12

R12,750 ZAR per night

Guest favorite

Vacation home in Raymond

5.0 out of 5 average rating, 13 reviews

Paradise Point on Panther Pond

Mar 17 – 24

R14,587 ZAR per night

Guest favorite

Guest suite in New Gloucester

5.0 out of 5 average rating, 13 reviews

Many Moons Farm

Sep 17 – 24

R1,238 ZAR per night

Guest favorite

Guest suite in Pownal

4.97 out of 5 average rating, 73 reviews

Maine Mystic Gardens, Family Friendly Suite

Dec 17 – 24

R2,060 ZAR per night

Guest favorite

Home in Windham

4.95 out of 5 average rating, 64 reviews

Waterfront Gem walkable to Restaurants!

Nov 28 – Dec 5

R3,933 ZAR per night

Guest favorite

Home in Raymond

5.0 out of 5 average rating, 7 reviews

Cozy Cottage in Raymond

Sep 1 – 8

R4,410 ZAR per night

Superhost

Home in Casco

4.82 out of 5 average rating, 44 reviews

Fully Updated Lake View Home on Thomas Pond

Jun 22 – 29

R7,087 ZAR per night

Guest favorite

Home in Gray

5.0 out of 5 average rating, 18 reviews

Little Sebago Lakefront Getaway

Oct 30 – Nov 6

R4,569 ZAR per night

Show all

Quick stats about vacation rentals in Raymond

Total rentals
290 properties
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Pet-friendly rentals
90 properties allow pets
Family-friendly rentals
220 properties are a good fit for families
Total number of reviews
5.9K reviews
Nightly prices starting at
R957 ZAR before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Raymond?
Yes! Work meets play with ease at over 130 vacation rentals in Raymond featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Raymond?
Four-legged friends are welcome in Raymond. Choose from more than 90 vacation rentals for guests traveling with pets.
Are there family-friendly cabin rentals in Raymond?
Raymond has more than 30 family-friendly cabin rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cottage rentals in Raymond have a bbq area?
Absolutely! We offer over 50 cottage rentals with a bbq area in Raymond. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Raymond have wifi?
Absolutely! We offer over 30 cabin rentals with wifi in Raymond. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Raymond?
Experience the best of Raymond with our apartment rentals, starting at about $90 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 Raymond have a gym?
Absolutely! We offer over 10 house rentals with a gym in Raymond. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Raymond have air conditioning?
Absolutely! We offer over 40 cottage rentals with air conditioning in Raymond. Enjoy a tailored experience with all the comforts you desire.

Raymond vacation rentals

Top-rated vacation rentals in Raymond

Vacation rentals for every style

Cottages

Cabins

Houses

Popular amenities for Raymond vacation rentals

Stay near Raymond's top sights

Other great vacation rentals in Raymond

Guest suite in Lewiston

Apartment in Casco

Cottage in Raymond

Cottage in Raymond

Home in Raymond

Apartment in Gray

Cottage in Windham

Cottage in Raymond

Other great vacation rentals in Raymond

Home in Raymond

Vacation home in Raymond

Guest suite in New Gloucester

Guest suite in Pownal

Home in Windham

Home in Raymond

Home in Casco

Home in Gray

Quick stats about vacation rentals in Raymond

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 vacation rentals with a dedicated workspace in Raymond?

Are there pet-friendly vacation rentals in Raymond?

Are there family-friendly cabin rentals in Raymond?

Do cottage rentals in Raymond have a bbq area?

Do cabin rentals in Raymond have wifi?

How much does it cost to stay in apartment rentals in Raymond?

Do house rentals in Raymond have a gym?

Do cottage rentals in Raymond have air conditioning?

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